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enolate formation from calcium carbide?

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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?

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

Post 455083 (ning: "Questions about drone's enolate p2p synth", Newbee Forum)

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

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.

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

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?


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