Author Topic: cl2 + koh + iso = mdp2p  (Read 11659 times)

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  • Guest
Re: cl2 + koh + iso = mdp2p
« Reply #60 on: November 29, 2001, 01:00:00 AM »
i've been wondering about this procedure for a while
qi how much isosaassay to ghow much dcm and how manyt g'g of chlorine gaas should be aded ifd usinfg 100gf safrole.
2. then distrill off dcdm relux wirth aquous 15% koh for ? hours extract with dcm and dsistill mdp2p.
any ideasa
soundes verey orc to me

i don't worry about the 4 letter words, its the letter words i despise!


  • Guest
Re: cl2 + koh + iso = mdp2p
« Reply #61 on: November 29, 2001, 02:46:00 AM »
Wow, that post by uemura is nice, it's not exactly the same, but uses br2 and isosafrole.  If anyone is wondering it's post

Post 236632

(uemura: "Re: Ketones from Propenylbenzenes via the di-bromides", Novel Discourse)
.  As far as developing the procedure using cl2, someone needs to balance out some equations.  Maybe later.


  • Guest
Chlorination with NaCl/H2O2
« Reply #62 on: December 10, 2001, 04:44:00 AM »
Phase Transfer Catalyst Promoted Halogenation of Alkenes with Hydrohalic and Acid Hydrogen Peroxide

Addition of molecular halogens especially that of gaseous chlorine, presents a potential environmental hazard and their quantitative utilization is often problematical. Chlorination of sulfanilamide with a mixture of aqueous hydrochloric acid and hydrogen peroxide has been reported, and recently the combination has been used for converting phenol to chloranil. These reactions might not have involved nascent molecular chlorine, but the in situ formation of a positive halogen species. In the light of this consideration, it seemed to be of interest to study the efficiency of the halogenation of olefins by this reagent system.

We wish to report the results of such an investigation using conditions similar to those of Lübbecke and Boldt. Furthermore, our investigations showed that the presence of a cosolvent (carbon tetrachloride) and catalytic quantities of phase transfer agent, such as benzyltriethylammonium chloride is beneficial, as the formation of chlorohydrins can be largely suppressed. These conditions are applicable to the preparation of dichlorides and dibromides, and give good, frequently better yields than the conventional halogen addition reactions.

It is noted that the ease of handling and regulation may render the method viable for laboratory halogenation, especially chlorination. Both gaseous chlorine and sulfuryl chloride could induce side reactions involving free radicals, which are not observed under our ionic conditions.

Halogenation of Alkenes; General Procedure:

To an ice-cooled, magnetically stirred suspension of the alkene (50 mmol), calcium halide (50 mmol), conc, hydrohalic acid (10 ml), carbon tetrachloride (10ml), and benzyltriethylammonium chloride (100 mg) is added dropwise 30% hydrogen peroxide (6 ml). The mixture is then allowed to warm up to room temperature while stirring is continued for 20 min. Dilution with petroleum ether, washing with water, drying and removal of solvent, gives the crude dichloride or dibromide which is devoid of starting alkene as shown by infrared spectral analysis. Purification of the product by vacuum distillation furnished by sample identical in physical and spectral properties to the authentic compound.

Chlorination: cyclohexene (76%), 1-octene (56%)

Bromination: cyclohexene (95%), 1-octene (92%)

Reference: Synthesis 676 (1977)


  • Guest
Re: Chlorination with NaCl/H2O2
« Reply #63 on: December 10, 2001, 09:54:00 AM »
Aminator will committ to such meanial tasks. ;) 'tis good practice.
34.5% HCl = 1.1L/1mole
4.5% (chlorox)sodium hypochlorite=1.7L/1mole
2 HCl(aq) + NaOCl(aq)----->  Cl2(g) + NaCl(aq) + H2O(l)

I hope the % solutions are correct.


  • Guest
Re: Chlorination with NaCl/H2O2
« Reply #64 on: December 10, 2001, 03:21:00 PM »
Conc. HCl is more like 11-12mole/l.


  • Guest
« Reply #65 on: July 06, 2002, 09:25:00 PM »
Has any more work been done with this?

over and under, then back to the start
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