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Author Topic: Interchangability of Ether and Hexane  (Read 165 times)

sloppy

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Interchangability of Ether and Hexane
« on: June 06, 2012, 05:05:17 PM »
Hi, long time no see.
Quick question that concerns if hexane can be swapped with ether or not. Some searching revealed they may be similar enough to work but...doesnt hurt to ask especially if someone knows the answer and saves me a waste of time.

Reaction concerns potassium ethoxide, toluene and ethyl acetate to P2P. I have to admit its from Festers' book. The reaction is done in anhydrous ether. I have about 600ml homemade ether left which can be made anhydrous, but the apparent saving of time and ease of using anhydrous hexane instead of dry ether is appealing.

So..I humbly ask, does anyone have knowledge of this?  reduced product? outright failure?
Thanks

lugh

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Re: Interchangability of Ether and Hexane
« Reply #1 on: June 06, 2012, 08:00:32 PM »
The reaction that Fester claims to work in ether fails, so it's not very likely to work with hexane either:

https://the-collective.ws/forum/index.php?topic=9535

most of what Uncle Fester writes is what knowledgeable bees such as drone342 and Assholium called chemical pulp fiction  ::)  Don't waste resources and time on such drivel  :-X  As always, the end results from the effort applied  8)
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sloppy

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Re: Interchangability of Ether and Hexane
« Reply #2 on: June 07, 2012, 07:49:15 AM »
fresh1 - 'howz you K supply?'...fine, actually. Most stored in oil, soon to be monkeyed-around with K is under kerosene unless I change my mind and put it back under oil. WTF would you put it in H20 for?

If you want some Sodium, I have a few pounds of which I occasionally cut off a block of 20 grams (4x4 inch block anyway) or so and throw in the beaver pond out back to scare the shit out of the local wildlife while amusing myself...not related to anything here, just yabberin'...

Anyway....Substituting hexane for ether is immensely more available and easier to make anhydrous. Its a pain in the ass to make ether. A bigger one to make anhydrous. By 'pain in the ass' I mean time to make...as compared to buying a gallon jug of hexane at the local supply store.

Orgsyn was referenced but I wasnt at my notes/puter so I mention Fester 'cause I knew it was there somewhere...and BOY does his name get attention! lol.
But just because I mention Fester doesnt mean I consider it the holy grail of anything. But it has ideas if not much else. So does alot of other sites. But as far as the 'pulp fiction' goes, some work most dont.. but it points me where to go look for it from references. Or what to inquire about or ask, at least.
But Orgsyn, or nearly anywhere else, isnt going to outright state "ok to swap this with that" for obvious reasons. So...I asked!

Lugh, I followed your link, actually forgot I was a member there. The reason I asked was, as asked, to save time/waste of it.
Potassium enolate..ethyolate(sic) ok, I thought it was potassium ethoxide..prolly confused it with sodium ethoxide I read somewhere else...but like I said..going by memory, or trying to, gets rougher the older I get...
Thanks.

edit- Lugh, thanks for that collective orgsyn reference. Fuck that Fester! lol. Nowhere idd he mention a Parr hydrogen apparatus!! "oh sure, I have one out back." yeah...
« Last Edit: June 07, 2012, 07:59:44 AM by sloppy »

atara

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Re: Interchangability of Ether and Hexane
« Reply #3 on: June 09, 2012, 07:18:22 PM »
Ethyl acetate is more acidic than toluene, so it'd be more likely to just alkylate itself under those conditions anyway... and it does, of course...

fresh1

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Re: Interchangability of Ether and Hexane
« Reply #4 on: June 10, 2012, 03:21:12 AM »
sloppy my sincerest apologies :-[  I actually thought you we're spinning shit so I thought I'd test you with the K/H2o ;)  Ooops! ::)

welcome to this place matey, I'm completely jealous of someone who has a few pounds of sodium lying around :o AND potassium (in kero ;D)

fuck me I'm lost for words at this point ???
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carl_nnabis

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Re: Interchangability of Ether and Hexane
« Reply #5 on: June 10, 2012, 09:10:53 AM »
why do they keep people away from buying such harmless stuff like potassium and sodium? I have just recently read about some fifteen year old few minutes ago in a german chemistry board who fused both metals just for fun and entertainment at home  :o I mean it isnt toxic stuff or anything like lithium is?
"It's like the drug trip I saw when I was on that drug trip!"

fresh1

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Re: Interchangability of Ether and Hexane
« Reply #6 on: June 10, 2012, 04:05:14 PM »
I believe safety factors restrict sales down here :-\  And that they're hard to come by (disceretly :D) is an understatement

You germans have all the fun :P
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carl_nnabis

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Re: Interchangability of Ether and Hexane
« Reply #7 on: June 11, 2012, 02:28:00 AM »
this is actually funny that you mention transport restrictions, because i know someone who bought sodium somewhere from eastern europe in some former soviet state (it was reallyreally cheap thats why), and it came just wrapped in aluminium foil  :o
paraffin oil? fuck that, no need for that stuff in lithuania! ;D
"It's like the drug trip I saw when I was on that drug trip!"

sloppy

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Re: Interchangability of Ether and Hexane
« Reply #8 on: June 22, 2012, 04:37:31 PM »
Man..its seeming a grignard w/acetonitrile may be best way...I wonder if I can get in a summer chem class just to get the prof to do a grignard???... may be easy to some but it dont to me...I did see on youtube some class making phenylacetic acit from co2 in a grignard...I wonder if someone posted with acetonitrile?? lol

carl_nnabis

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Re: Interchangability of Ether and Hexane
« Reply #9 on: June 22, 2012, 06:33:04 PM »
Quote
I wonder if someone posted with acetonitrile??
I have never heard of it before, of course would be way funnier to use that instead of acetaldehyde or acetaldehyde-methylimine ;D
I am a bit lazy too look now and not so familiar with nitrile and cyanide chemistry, does the addition product of benzyl chloride and acetonitrile already hydrolyze to the amine? or is there another reaction involved (sounds more logical to me) in which for example a n-methyl group could be substituted?
If so, then maybe substitution with a n-ethanol-2-ol-amine instead of a n-methylamine group would lead (benzyl chloride replaced with benzoyl chloride) to hydroxyethyl-norephedrine... for phenmetrazine ;D
Quote
..its seeming a grignard w/acetonitrile may be best way...
yeah pretty cool one! seems to me either! *pours honey around everywhere*
"It's like the drug trip I saw when I was on that drug trip!"

Sol Invictus

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Re: Interchangability of Ether and Hexane
« Reply #10 on: July 02, 2012, 10:48:36 AM »
In Sol's imagination, yields were always lower than expected w the aforementioned Grignard w BzCl, even w N2 inert atmosphere & careful monitoring of the rxn. Yield increased a bit w isolation of the BzMgCl prior to addition of MeCN, but said isolation was quite a chore & yield went up only like ~10% (~40% was highest ever, got ~20% w/o isolating the Grignard intermediate). I would recommend fresh distillation of the BzCl & purification of all solvents prior to attempting the Grignard & make sure everything is DRY AS FUCK. Of course yr mileage may vary.
 Oh & something comes to memory about polymerization occurring when trying to vac. distill the ketone due to residual byproducts coming over after the HCl hydrolysis, so perhaps a Na bisulfite adduct formation might be wise vs. just going straight for the distillation.
Best of luck- watch out for the BzCl vapors, it's like being tear gassed...
« Last Edit: July 02, 2012, 10:52:51 AM by Sol Invictus »
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