Author Topic: enolate formation from calcium carbide?  (Read 3421 times)

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stratosphere

  • Guest
enolate formation from calcium carbide?
« on: December 10, 2003, 09:46:00 PM »
calcium carbide is a very strong base (not quite MeLi, but lots stronger than hydroxide) that also happens to be readily available in bulk...

it would seem reacting it with acetone would drive off acytelene (indeed just going by pka's the pka of acytelene is 25 and that of acetone is 19, so its plenty strong to deprotanate acetone) and yield the enolate of acetone, which should do fun stuff with phenylhalides...

so if it were really this easy, why have i not found anything in tfse about this method?

java

  • Guest
RE: Enolate acetone.....
« Reply #1 on: December 10, 2003, 11:18:00 PM »
Just recently Ning had some coverage on the enolate process and there were many references and posts associated with it , which you might try to check out.....java

Post 455083

(ning: "Questions about drone's enolate p2p synth", Newbee Forum)


Note: Potassium tert-Butoxide  is another material available to enolate acetone.....so the literature says.


stratosphere

  • Guest
i suppose if using calcium carbide directly to
« Reply #2 on: December 11, 2003, 11:12:00 PM »
i suppose if using calcium carbide directly to produce acetone enol was unacceptable for some reason,
the CaC2 could be reacted with t-butanol to form calcium butoxide, this reaction would almost certainly be quicker and simpler then antochos otc alkoxide synth.
with CaC2 only costing ~$10(us)/lbs it would certainly seem a worthwhile thing to experiment with.

java

  • Guest
RE: Enolate acetone.....
« Reply #3 on: December 12, 2003, 12:30:00 AM »
stratosphere......I think your theory could work but as to the solvent to use since it states in the process to use ammonia, since I don't know what it's function is, I imagine an excess of calcium butoxide , since it will keep the enol active to react with say Halobenzene to produce ......

ArX  +   CH3COCH3*  ---------> ArCH2COCH3 + ArCH2CHOHCH3
* acetone enolate

this of course would be great since acetone and CaC2 and the material to make the Halobenzene are pretty much OTC this would be one step closer to an easy method for P2P synthesis.......java


stratosphere

  • Guest
i could not find any direct information on the
« Reply #4 on: December 12, 2003, 01:33:00 AM »
i could not find any direct information on the reaction of CaC2 with alcohols, but i did see alchol as well as water listed as incompatiple with it, which would seem to indicate that indeed the alkoxide and acytelene do form, also from the pKa value it is evident that CaC2 is a stronger base then t-butyoxide.

i think for the solvent an excess of acetone would be used.

what is t-butanol sold otc for?

algebra

  • Guest
ammonia
« Reply #5 on: December 12, 2003, 04:51:00 AM »
you dont need ammonia!! - use dmso - read the refs drone posted.

java

  • Guest
RE: Enolate acetone.....
« Reply #6 on: December 12, 2003, 04:52:00 AM »
I would say about $80 dol/gallon.....not a bad investment to work on a dream that may have some honey of a result.......java


acx01b

  • Guest
what to say about CaC2 ?
« Reply #7 on: November 13, 2004, 12:23:00 AM »
what to say about CaC2 ?
i bougth some in france 10Euros 800grams, looks good quality (more than 90% purity) but not 99% (weird things not dissolving in water after reaction with water)

it is a strong base? why it doesn't work to dry some diethylether then ?
(is it new to you that CaC2 doesn't work to dry ether?)

enfin: CaC2 doesnt appear to react with acetone at all