Preparation of 15-hydroxypentadecanoic acid by means of condensation reaction via β-ketosulfoxide
- 1 December 1968
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 46 (23) , 3767-3770
- https://doi.org/10.1139/v68-625
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 14-pentadecenoic acid (13) in a 38% overall yield based on the undecenoate.Keywords
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