G. M. Rubottom, J. Gruber, K. Kincaid
Jun 15, 1976
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Journal
ChemInform
Abstract
Abstract Standard methods for the preparation of phenacyl acetate include the acetolysis of both α-diazoacetophenone1 and α-bromoace-tophenone2, as well as the treatment of acetophenone with lead tetraacetate (LTA) in refluxing benzene3. We should like to report that trimethylsilyl enol ethers, 1, react with LTA at room temperature in benzene to afford, after hydrolysis, excellent yields of aryl substituted phenacyl acetates, 2 (Equation 1). In terms of both yield and mildness of reaction conditions the method is to be recommended over current literature procedures. The ready hydrolysis of 2 into α-hydroxyketones, 3, serves to further extend the synthetic potential of the method4,5 (Equation 2). The data in Table 1 summarize the results of the oxidation reaction.