Dakin-West synthesis of beta-aryl ketones.
Triethylamine and 1-methylimidazole were found to be selective catalysts for the Dakin-West synthesis of diaryl ketones and aryl methyl ketones, respectively. In the 1-methylimidazole-catalyzed reaction, catalysis is due to the simultaneous formation of both an effective acylating agent, 1-acyl-3-methylimidazolium, and a base, carboxylate anion. Hydrocinnamic acid, a compound previously reported to be unreactive under Dakin-West conditions, forms 4-phenyl-2-butanone when the reaction is catalyzed by 1-methylimidazole.
Tran
Khanh-Van
KV
Department of Chemistry, Smith College, Northampton, Massachusetts 01063, USA.
Bickar
David
D
D019342:Acetic Acid / Q000737:chemistry; D000089:Acetic Anhydrides / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D000812:Anhydrides / Q000737:chemistry; D002384:Catalysis; D007093:Imidazoles / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D010648:Phenylacetates / Q000737:chemistry
D000089:Acetic Anhydrides; D000596:Amino Acids; D000812:Anhydrides; D007093:Imidazoles; D007659:Ketones; D010648:Phenylacetates; C031800:acetic anhydride; C025136:phenylacetic acid; C018100:1-methylimidazole; D019342:Acetic Acid