benzyl chloride from hypochlorite salts

[Satan]

Can anyone suggest ideal reaction conditions for the toluene + hypochlorite --> BzCl reaction?

[tecnetium]

I too have an interest in benzyl halides! There are details about this reaction in Rhodium's site under P2P's from benzene / toluene. It invloves heating toluene with NaHCLO3 to apparently give benzyl chloride in good yeilds- the description is very breif though.

[CHEM_GUY]

On the old Board there was a thread called OTC Benzyl Chloride which someone named "ymir" detailed this procedure. 
I looked on the old board and did a search, but the post was lost.

From what I remember he/she dryed the toluene and the calcium hypochlorite then added an excess of the Ca(OCl)2 and heated it, careful not to explode the mixture.  If i remember there was addition of light as well. 

Ymir didn't detail the drying of the Ca(OCl)2, but said he had to dig up some old references.  By the way, drying Ca(OCl)2 is dangerous.

Read my Disclaimer: 

http://cantsueme.homestead.com

[CHEM_GUY]

I found the old thread "OTC Benzyl Chloride" on the hive.txt zip files from Wizard X.  Here is the repost:

Author Topic:   OTC Benzyl Chloride
            ymir
            Member  posted 07-04-99 03:40 PM          
           
            Tales of Jotunheim-I
            The frost giants were getting restive. Summer was coming, and their
            ice supply was dwindling. Loki, having tired of the tank, and its
            difficulties, decided to give USP 1280612 a try. He thanks Spiceboy
            for publicizing it, and Scooby for posting his problems with it.
            Many details were missing, so Loki did his homework, and discovered
            that about twenty years ago, in the interests of making HTH
            foolproof, Olin-Matheson ceased completely drying HTH. Loki
            determined that dry HTH was stable up to at least ninety degrees
            fahrenheit, and that in days of yore, before commercial
            availability, had been dried in the laboratory for six days in the
            dark, in a dessicator using an oil pump. Loki tared the weight of
            the calcium hypochlorite in a three pound HDPE margarine container,
            gently placed it in his vacuum dessicator, covered it with an old
            towel, and started the pump. Periodically, Loki checked the weight
            of the HTH under low illumination. By the next day, the HTH ceased
            to lose any more weight. The lid was placed on the dry HTH to keep
            it that way. Commercial toluol was distilled, a fresh dry flask
            being attached after the temperature reached 110 degrees
            centrigrade. After distillation was finished, the dried toluene was
            poured into an acetone dried wine jug, along with a few ounces of
            anhydrous magnesium sulfate. Loki then assembled his chlorination
            apparatus. A 5L flask filled with 1365 g of dry HTH and 1575 ml of
            toluene, fitted with a thermometer and a condenser, with the end of
            the condenser filled with dried cotton and anhydrous calcium
            chloride. A stopper was inserted into the end of the condenser, with
            fuel line connecting sequentially to two gallon jugs, the first
            empty, with a stopcock, and the second filled with tap water. A
            polyethylene milk jug filled with washing soda solution, cut out to
            accomodate a funnel completes the gas adsorption apparatus. The oil
            bath was heated up slowly to 85 degrees, and a heat lamp was then
            directed into the flask. The exothermic reaction proceeds best
            around 105 degrees, so the heating bath must be kept cooler until
            the end of the reaction. HCl gas begins to bubble out of the
            toluene. Once the reaction temperature reaches 105 degrees, the heat
            lamp is turned off. It is well to wire down the empty jug's stopper,
            and to use the stopcock to release the vacuum, when necessary. After
            a few hours of slow bubbling, a rapid evolution of HCl will occur.
            This will be absorbed by the apparatus. The stopcock is used toward
            the end of the reaction, to prevent sucking back, and at other times
            while adjusting the heat. The liquid is decanted, and the solids
            filtered under vacuum. The excess toluene is distilled, and then
            three pints of 99% isopropyl alcohol is added (at least 1230ml), to
            deal with the toluene/benzyl chloride azeotrope. The
            toluene/isopropanol azeotrope distills at 80.6 degrees centrigrade,
            and then the excess isopropanol distills at 82.4 degrees
            centrigrade. The benzyl chloride was then distilled using a Perkin
            triangle (Vogel's), with a glass packed claisen head, to change
            flasks without releasing the vacuum on the distillation flask.
            Depending on the strength of the vacuum, the benzyl chloride
            distills somewhere around 100 degrees centrigrade. The yield is
            around 500 ml, which may be dried with anhydrous calcium chloride or
            5A molecular sieve, if it is to be used in a Grignard. The toluene
            may be recovered from the azeotrope by flooding it with water, the
            toluene will seperate. However one chooses to execute this, no iron
            should contact benzyl chloride, as it will catalyze decomposition.
            Scooby Doo
            Member  posted 07-06-99 08:01 PM          
           
            That is an excellent piece of work if do say so myself. Loki you
            most definitely have bigger balls than I on drying the hypochlorite,
            good call. The yield is sensational, but I noticed that Loki used
            commercial grade toluene. I have dreamed of cleaning commercial
            grade toluene via Vogel (Thanks again jimwig) of thiopenes (sp?). I
            dreamt of being totally surprised on the amount of crap that the
            sulfuric acid wash removed, with yields following suit and going up.
            I know what you mean in regards to the azeotropes, I tended to see
            this with water and benzyl chloride distilling over at 80 deg.
            However the distillate would quickly break down (minutes) due to the
            water.
            Its interesting to see that Loki still experienced the violent
            reaction with the massive amount of HCl being released. I would have
            thought anhydrous conditions would have gotten rid of this problem.
            I have dreamt of multiple runaway reactions which tended to get very
            violent. When one empties the flask one can see stones, which are a
            brown/black colour where the reaction took place. I believe mixing
            might get rid of this localised reaction and keep it more steady.
            Its probably due to the HCl being hygroscopic and collecting water
            out of the atmosphere which inturn reacts with the Calcium
            hypochlorite.
            Scooby
           
            ymir
            Member  posted 07-06-99 08:20 PM          
           
            Loki doesn't think that it is water, he says the gas observed was
            definitely HCl. Loki thinks that its just the course of this
            particular reaction to go bananas at a certain point. The apparatus
            described can deal with this easily, and could be scaled up further.
            He says its vital to have a drying agent in a tube, or the end of
            the condenser. Loki is aware of the thiophene removal technique,
            half of what he knows he got from Vogel's. Next time, he'll try it.
            Loki says the tank method won't even work well with thiophene left,
            so this method is superior in more than one way.As far as drying
            HTH, its in Inorganic Syntheses, Vol. 3; as long as the temperature
            and light level constraints are observed, its absolutely safe. Its
            been almost a hundred years since any one had to do this, so digging
            was necessary. Methanol will remove the toluene also, buts its
            azeotrope is only 25% toluene, instead of 42%. Now its on to the
            next battle, OTC P2P!
            Loki
            Member  posted 07-07-99 02:01 AM          
           
            Me? I havent even started looking at first rxn yet.....  still
            learning verry basics....But with a name like Loki its got to be
            good
            ------------------
            It aint got a thing if it aint got that swing...
            ymir
            Member  posted 07-07-99 04:03 AM          
           
            They say imitation is the sincerest form of flattery, so please try
            to keep yourself under control. Someone who is not ymir, known as
            Loki (not to be confused with this newbee), wants the Hive to also
            know that everything used in this procedure must be clean! Certain,
            unknown as of yet organic and inorganic materials have intiated the
            explosive decomposition of calcium hypochlorite, and thus, as usual,
            cleanliness is next to not only godliness, but additionally,
            ungodliness. Also, the reference, Kirk-Othmeyer, states that HTH is
            dried at 90 degrees Centrigrade, so any environmental temperatures
            should be safe. Another factor that Loki wants the Hive to know is
            that Loki has the distinct feeling that sunlight (with its UV) is
            the main initiator of these explosions, so appropriate precautions
            must be taken.
            ymir
            Member  posted 07-07-99 06:23 AM          
           
            Loki also wants to point out that the heat lamp used was an
            infra-red lamp.
            Rhodium
            Administrator  posted 07-07-99 06:04 PM          
           
            Where can I find the original patent text, as well as a write-up of
            Scooby's adventures? I'd like to put this on my page.
            ymir
            Member  posted 07-08-99 08:34 AM          
           
            Old US Patents are available from the Patent Office in Washington,
            D.C.; and the older Patent Depository Libraries:
            University of the State of New York, Albany, NY
            Georgia Institute of Technology, Atlanta, GA
            Boston Public Library, Boston, MA
            Grosvenor Library, Buffalo, NY
            Chicago Public Library, Chicago, IL
            Cincinatti Public Library, Cincinatti, OH
            Cleveland Public Library, Cleveland, OH
            Ohio State University, Columbus, OH
            Denver Public Library, Denver, CO
            Detroit Public Library, Detroit, MI
            Linda Hall Library, Kansas City, MO
            Los Angeles Public Library, Los Angeles, CA
            State Historical Society Library, Madison, WI
            Milwaukee Public Library, Milwaukee, WI
            Minneapolis Public Library, Minnieapolis, MN
            Newark Public Library, Newark, NJ
            New York Public Library, New York, NY
            Franklin Institute, Philadelphia, PA
            Carnegie Library, Pittsburg, PA
            Providence Public Library, Providence, RI
            St. Louis Public Library, St. Louis, MO
            San Francisco Public Library, San Francisco, CA
            Seattle Public Library, Seattle, WA
            Oklahoma State University, Stilwater, OK
            Toledo Public Library, Toledo, OH
            Obviously, the first places to look in Europe would be at Oxford,
            the Sorbonne, Berlin, Rome and Moscow.
            Rhodium
            Administrator  posted 07-08-99 07:39 PM          
           
            You silly, I can order any patent from the university library, I
            just thought I could save the $10 fee, as well as a lot of work if
            you could provide me with the essential parts of the patent, as you
            obviously have a copy of it yourself.
            ymir
            Member  posted 07-08-99 08:53 PM          
           
            Actually, as I indicated in the E-mail I sent you, I don't have a
            copy of the patent.
            CHEMMAN
            Junior Member  posted 07-22-99 05:37 AM          
           
            Am dreaming of chlorinating toluene with gas Have Vogel-any further
            advice on cleaning up the toluene that he doesnt mention,as even
            though I have supposedly high grade toluene,am not convinced.Thanks
            for any help!
            CHEMMAN
            Junior Member  posted 07-22-99 05:42 AM          
           
            Sorry for the double post ,but what does HTH stand for
            ?hypochlorite?? Sorry for the ignorance too !! CheersCHEMMAN
            ymir
            Member  posted 07-22-99 07:07 AM          
           
            HTH is Olin-Mathesonspeak for calcium hypochlorite!
            Scooby Doo
            Member  posted 07-24-99 07:37 PM          
           
            Rodium here is the abstract ref which might help (CA 1918 vol.12
            (nov-dec) p2573)
            C.C. Loomis U.S. 1,280,612, Oct 1. In chlorinating toluene to form
            benzyl chloride, the toluene and dry bleaching powder are heated
            together to a temp. of about 105 deg in the absence of acid or other
            reagent for decomposing the bleaching powder. This treatment avoids
            the formation of by-products, if about equal amounts of toluene and
            bleaching powder are used. Larger proportions of bleaching powder
            effect more complete chlorination of the toluene but produce also
            other products such as benzal chloride and benzotrichloride.
            There was no write up on my behalf of this reaction, just a lot of
            mistakes. Ymir has definitely done the hard yards with this reaction
            getting it up and running.
            Ymir I was interested to hear the use of an infra red lamp, I always
            believed that UV is what helped the normal method of chlorine gas
            chlorination of toluene. I can totally agree with you on the non use
            of any UV lamps around kwazy chlorite, but why the infra red?
            Scooby
           
            ymir
            Member  posted 07-25-99 02:41 AM          
           
            Loki says the heat lamp raises the temperature to the required 105
            degrees, then is shut off, because the reaction is exothermic! Using
            only one heat source (oil bath) causes the reaction to get too hot!
            Scooby Doo
            Member  posted 07-25-99 07:34 PM          
           
            Yeah I know what you mean, reactive little sucker!
            The acetaldehyde + BzCl is looking promising, the caustic smelling
            oil (suspected P2Pol) from the above reaction was oxidised using
            Sodium Dichromate in H2SO4 yielding a very sweet smell indeed. I
            will hopefully dream some more on this soon.
            Scooby

Read my Disclaimer: 

http://cantsueme.homestead.com

[hellman]

This must get sorted out,

We are all so close,
We must stay on target with route for p2p,.
Let me digress,.
----------------------------------------------------------
stage one:
Toluene to benzyl chloride
Progress Report:
Two main routes that are OTC viable, but lacking real world experimntation, or are we,.
Toluene-----BzCl2  via direct cl2 with uv(less OTC)
Toluene-----BzCl2  via hypochlorite(more OTC)

Issues: Azetropes that form, real world experimental data
        Reactions are straight forward
---------------------------------------------------------
----------------------------------------------------------
stage two:
benzyl chloride to Benzaldehdye
Progress Report:
This baby is completly sorted
There are many systems to chose from here
Issues: None
----------------------------------------------------------
stage three:
Benzaldehdye to Phenyl Nitropropene
Progress Report:
This baby is completly sorted
There are also many systems to chose from here, but mainly the nitroethane seems to work nicely
Issues: None
---------------------------------------------------------
stage four:
Nitropropene to p2p
Progress Report:
This baby is completly sorted
There are many systems to chose from here in good yield
Issues: None
----------------------------------------------------------
stage five:
animation of p2p
Progress Report:
This baby is completly sorted
There are many systems to chose from here
Issues: None
----------------------------------------------------------

So really to manufacture large amounts of this product,.
We need some good solid practical write-ups of turning
Toluene in to BzCl2,
Once we have this, and all the issues with azetropes sorted we will succeed,.
I am suprised that there have been oh so few posts regarding this particular method,
Obviously i can only assume that this particular proceedure is well protected, and close to the hearts of many,.

But fortunately that is why we are here,
I would like to see plenty of successfull synths starting from toluene to make Bzcl2, preferably starting from
HTH,.
Join with me, and soon we can have what we once had not,.
Is it not that obvious to my fellow bees that this is enevitable, toluene-bZcl2-benzaldehyde-nitropene-p2p-amine,

Or even more elusive, the nitropene-urusla-amphetamine-meth,.

*Dumb and final question, what can we through into a nitropropene eating Ursibara, that will give meth not amphetamine,.?

hellman

[Data]

Don't let it get over 105c (BIG BANG)

[Data]

One more thing if i was going to do this i would do it in someones house that i really hated. Or if i had no one to hate in the middle of a paddock. When it goes. it throws glass up to 50 metres. My friend done this synth and didnt keep an eye on the thermonitor he said he turned a way for a minute to do something when he looked back the hypochlorite powder was bubbling heaps as he reached over to turn it off it all started to fizz and pop as flames appeared in the 4ltr bottle full with tol so he ran as quickley as possibale to get the hell out there but as he got 4metres away it went bang(big bang) He got a peace of glass stuck in the left side of his stomach and glass was impreginated in the walls with a big black cloud of smoke.  
The second time he did this he noticed that the tempreture in the oil bath was 20c lower than the Cl powder in the bottle maybe this was heated to quick. Anyway he did the same thing looked away and too many bubbles were comming out of the hypochlorite powder as he ran to turn off power it went pop bang (not as big as the first time) and flames were touching the ceiling and the hose wouldnt reach the fire he really shit himself.
             So watch that temp.

[halfapint]

The easy way to make benzyl chloride is with a glass coffeepot filled with equal weights (not equimolar weights) of toluene and chlorine pool shock, Ca hypochlorite. The tablets work OK, though the huge biscuit type, if you get those, probably should bee broken up a bit. Expose one at a time to the air, and bust it quickly with a hammer, before it gets water out of the air. Use a water bath to allay your fears about thermal runaway, unless your heat source will reliably keep the rxn under 100°. Stretch plastic wrap over the lid of the coffee pot, to keep from losing too much toluene to evaporation. I think the actual knee of thermal runaway is the 113° boiling point of toluene, but as has been emphasized above, give it some margin. I like to keep it below 100°, myself: I don't mind spending a bit more time in the reaction to avoid breaking glass, even if it is only a Goodwill coffeepot.

This one is for outside, unless your fume hood gives you nerves of steel. Note that simply changing the proportions of Ca hypochlorite to toluene, from 1:1 by weight to 1.5:1 or as I prefer 1.66:1, will give you a product containing an increased proportion of benzal chloride compared to benzyl chloride. Benzal chloride is conversible to benzaldehyde by simple acid or basic hydrolysis, though to get benzaldehyde from benzyl chloride needs a little oxidative boost, e.g. chromic acid. Also note that MnO2/aq H2SO4 will convert a mixture of both benzyl chloride and benzal chloride to benzaldehyde.

The fractionation of toluene, benzyl chloride, and benzal chloride is quite sharp, and gives no trouble determining when to take the fractions. I usually just take the tolly (amounting to 2/3 to 3/4 of the filtrate) off at atmospheric pressure first. Then vac is applied for the benzyl chloride and then the benzal chloride. The still dregs are largely the useless benzotrichloride, discard the dark remnant.

Just watch this one for ~ 4 hours, and it's not such a big deal. The moderate bubbling you see coming off the hypochlorite is the chlorination reaction, it is not the toluene boiling. If the toluene boils, write it off. Watch from upwind.  Benzyl chloride is a nasty irritant.

Post 304720

(SideArm: "Benzal Chloride, and Benzaldehyde's Hidden Power", Chemistry Discourse)

Post 36700

(CHEM_GUY: "Re: benzyl chloride from hypochlorite salts", Chemistry Discourse)

US 1280612

(http://l2.espacenet.com/dips/bnsviewer?CY=gb&LG=en&DB=EPD&PN=US1280612&ID=US+++1280612A1+I+)
a half a pints a half a pound a half a world a half a round
Sidearm n. Flask neck tube.

[hellman]

Thankyou, thankyou very much,.
Lets continue,..

So mno2/h2so4 Huh?, hmm and that will take care of the benzal and the benzyl, no need for slaked lime, hmm,.

I thankyou for your imput,
Where can we get more pertinent information of the mno2/h2so4 system, ratios etc,.

Your post contained information that is crucual to the undoing of this proceedure,
thankyou again,.

hellman

[halfapint]

To all whom it may concern:

 Be it known that I, CHAUNCEY C. Loomis, a citizen of the United States, residing at Syracuse, in the county of Onondaga and State of New York, have invented a new and Improved Process of Chlorinating Toluene, of which the following is a specification.

My invention relates to the chlorination of toluene with consequent production of benzyl chlorid and its related products, benzal chlorid and benzo trichlorid. This has heretofore been accomplished by passing chlorin gas through boiling toluene and also by admitting to a mixture of toluene and bleaching powder an acid gas to decompose the bleach with liberation of nascent chlorin.

Both these processes are subject to objections, the former because of the difficulties incident to handling the chlorin and the production of by-products of little value which are not readily separable from the product desired and the latter by reason of the inconvenience of generating and applying the acid gas and the gumming up caused by its reaction with the bleaching powder in the toluene. I have discovered, however, and my invention broadly stated consists in the application of the fact, that by heating to a high temperature an anhydrous mixture of toluene and bleaching powder, with thorough commingling, and without the use of any acid, the chlorination of the toluene is effected without any of the disadvantages incident to the processes above referred to. In the absence of any added water the chlorin from the bleaching powder seems to go directly to produce benzyl chlorid in the side chain without attacking the nucleus, even though the process is carried on in the presence of iron, as in an iron vessel.

   In carrying my invention into effect, dry bleaching powder (calcium hypochlorite, or other equivalent hypochlorite,) and toluene are mixed in proportions varying according to the extent of chlorination desired. For example, 200 kilograms of toluene are heated, as in a steam jacketed iron mixing kettle to a high temperature, say 90°. Dry bleaching powder is then slowly added to this, the temperature being gradually raised until it approximates the boiling point of toluene, which, of course, cannot be exceeded. When 200 kilograms of bleaching powder have been added the mixture is held at the high temperature attained, (i. e., to secure the best results, from 100° C. to 105° C.) for about one hour, or, until the reaction is effected, with continuous thorough mixing. The escape of toluene vapor during the operation may be prevented by means of a reflux condenser fitted to the mixing vessel.

   The resulting mixture is then cooled down and allowed to settle and as much oil as possible is siphoned off from the top. The oil left adhering to the lime residue is then removed by steam distillation and added to that siphoned off. In this way 200 to 210 kilos of oil are obtained, having a specific gravity of .910 to .960 at 20° C. and containing from 30 to 35 per cent. of benzyl chlorid and from 70 to 65 per cent. of toluene. These can then be separated by fractional distillation. A higher percentage of chlorinated product can be obtained by using a greater proportion of the bleaching powder. In this case, however, some benzal chlorid and benzo trichlorid will be formed. Or, if desired, sufficient bleaching powder may be added to convert all the toluene directly to benzal chlorid and benzo-trichlorid and the resulting mixture of lime and the chlorids can be converted into benzaldehyde and benzoic acid by boiling with water.

Having thus described my invention, what I claim as new and desire to secure by Letters Patent is:

1. The process of chlorinating toluene which consists in heating together an anhydrous mixture of toluene and bleaching powder without other admixture.

2. The process of chlorinating toluene which consists in heating together toluene and dry bleaching powder in the absence of acid.

3. The process of chlorinating toluene which consists in heating together toluene and dry bleaching powder in the absence of acid or other agent for decomposing the bleaching powder.

 In testimony whereof I have affixed my signature, this 15 day of October, 1917.

CHAUNCEY C. LOOMIS.

--------
A true and faithful copy, insofar as Acrobat hath brung it out to me, and OCR hath interpreted the scratchy and speckled text. Note the dated spellings of chlorid and such.

Modifications of Chauncey's technique for the coffeepot were done largely in the interests of safety. Letting reacting hypochlorite get overheated really is a bad idea, don't do it twice. Using the pillow-shaped pool tablets works all right, and performing the reaction without stirring works all right. At the end, there is a lot of unreacted hypochlorite left, which may be reused. Shake it around to sift off the chloride, hydroxide and chlorate formed, then transfer the cohesive tablets into an airtight container with tongs, to bee added to your next run.

The MnO₂/acid oxidation of either BzCl or BzCl₂ is documented only by a diagram in one of my old texts. When I learn how to write formulae for the new smiles applet, I could show you a duplicate, but it wouldn't prove much: on the left is a benzyl chloride molecule, the word "or", and a benzal chloride molecule, in the middle is MnO₂ and H₂SO₄, then on the right is benzaldehyde. I've done lots of reactions with no more guidlelines than that, and sometimes they work.

I find Chauncey's last sentence in the body of the patent to be provocative: "Or, if desired, sufficient bleaching powder may be added to convert all the toluene directly to benzal chlorid and benzo-trichlorid and the resulting mixture of lime and the chlorids can be converted into benzaldehyde and benzoic acid by boiling with water."  Old Chauncey was probably guessing when he said "all" the toluene could get converted by using enough hypochlorite, it might not be so. Also I have little reason to make more calcium benzoate. I'm building an electrolytic cell to reduce my current  excess of benzoic acid to benzyl alcohol, a much more useful substrate.
a half a pints a half a pound a half a world a half a round
Sidearm n. Flask neck tube.

[former_chemist]

Calcium benzoate isn't likely to be a reaction product.  The reaction with water generates a large amount of HCl which will convert calcium oxide/calcium hydroxide to calcium hypochlorite/calcium chloride.

Calcium oxide and benzoic acid react to form calcium carbonate and benzene when heated.

[moo]

> Calcium oxide and benzoic acid react to form calcium carbonate and benzene when heated.

I seriously wonder what kind of effort is needed to perform this 19th century reaction...

[Elementary]

I don't think that anybody should attempt this procedure unless they can be sure that the calcium hypochlorite and toluene are anhydrous !

Also commercial calcium hypochlorite (pool shock) contains appreciable amounts of calcium hydroxide and calcium chloride as well.

If like swim in the UK, one can purchase benzyl alcohol easily from photographic suppliers, the concentrated hydrochloric acid method

https://www.thevespiary.org/rhodium/Rhodium/chemistry/benzylchloride.html

should be safer.
John Lennon - Working Class Hero

[Polverone]

From

Chlorination of aromatic systems with trichloroisocyanuric acid under polar and free-radical conditions
Eric C. Juenge, D. A. Beal, W. P. Duncan;
J. Org. Chem.; 1970; 35(3); 719-722.

The bit about benzyl chloride:

"Reaction of Trichloroisocyanuric Acid with Toluene Using Benzoyl Peroxide as the Catalyst.--To 15.43 g (0.2 mol) of toluene mixed with 0.6 g of benzoyl peroxide and 100 ml of carbon tetrachloride was added 11.62 g (0.05 mol) of trichloroisocyanuric acid. The reaction mixture was refluxed for 3 hr and the cyanuric acid, which precipitated almost quantitatively, was removed by filtration. The resulting reaction mixture was distilled through a 16-cm Vigreux column to give 11.5 g (44%) of benzyl chloride, bp 179-180° (760 mm), n²⁰D 1.5420. The physical constants obtained were identical with those reported in the literature, and the infrared spectrum was identical with the spectrum of an authentic sample of benzyl chloride."

Chemistry is merely my hobby, so I'll leave it for others to suggest how this might be reworked without CCl₄.

(edit) Whoops, I just realized that even though this thread is about benzyl chloride, my post might belong elsewhere since it's not about hypochlorites. Sorry if I've violated protocol...

19th century digital boy

[Elementary]

Interesting, but it sounds like an even more explosive mix if things go wrong, plus you will need carbon tetrachloride.
John Lennon - Working Class Hero