Organic synthesis by the Pummerer reaction. II. Synthesis of. alpha.-hydroxy acid derivatives from. beta.-keto sulfoxides

S Iriuchijima, K Maniwa…

Index: Iriuchijima,S. et al. Journal of the American Chemical Society, 1975 , vol. 97, # 3 p. 596 - 599

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Citation Number: 36

Abstract

Abstract: The reaction of 0-keto sulfoxides with acetic anhydride in the presence ofsodium acetate gives in one step and high yields a-acetoxy acid thioesters which are transformed into various types of a-hydroxy acid derivatives. For example, W-@-tolylsulfiny1) acetophenone produces Sb-tolyl) 2-acetoxy-2-phenylthioacetate which is converted into mandelic acid on al-kaline hydrolysis, 2-acetoxy-2-phenylacetanilide on reaction with ...