This is a retread of the famous "much discussed but never done" Drone 342 enolate synth of P2P. Two of the big annoyances of this method are (1): the need for a strong base, and (2): the need for DMSO, a bothersome solvent to work with.
However, during recent studies on PTC technology, it struck ning that the pKa of acetone is pretty low, and would bee easily deprotonated under PTC conditions. Very likely chlorobenzene could be coerced into reacting under these conditions, and it is used as a solvent, should bee far less suspicious than bromobenzene. Has this been discussed or tried before?
Suggested procedure.
11.6 g acetone
11.3 g chlorobenzene (or 15.7 g bromobenzene)
16 g NaOH
1 g or so Na2CO3 to keep NaOH from wadding up
100 mg PTC like alkyl benzyldimethylammonium.
Grind NaOH and Na2CO3 together until powdered and well mixed. Place in 100 ml RBF and stir like a mofo at R.T. for a few hours to a day, then evaporate acetone and dilute mixture with water, and the P2P should seperate out. Distillation {may} be required, depending on the degree of overalkylation/aldol condensation that occurs. Perhaps a hydrolytic workup would undo some aldoling.
C6H5-Cl + CH3C(=O)CH3 --PTC--> C6H5-CH2-C(=O)-CH3
as well as
(Ph)2CHAc
(Ph)3CAc
Typically, PTC has less multiple alkylation than a corresponding strong-base reaction, if I am to believe what I read. That is good.
Could this work?