Preparation of 15-hydroxypentadecanoic acid by means of condensation reaction via β-ketosulfoxide

H Nozaki, T Mori, M Kawanisi

Index: Nozaki,H. et al. Canadian Journal of Chemistry, 1968 , vol. 46, p. 3767 - 3770

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Citation Number: 11

Abstract

Basic condensation of 1, 12-dodecanolide with methylsulflnylcarbanion (DMSO-) gives a β- keto-sulfoxide 2 which is ethoxycarbonylmethylated and the product is converted to 15- hydroxypentadecanoic acid (6) in a 46% overall yield based on the lactone. Another β- ketosulfoxide 9 is prepared by condensation of methyl 10-undecenoate with DMSO-and is subjected to the Michael condensation with methyl acrylate. Treatment of the adduct gives ...