Simmons‐Smith reaction of allylic hydroxylated long chain α, β‐unsaturated esters
- 1 October 1980
- journal article
- Published by Wiley in Journal of Oil & Fat Industries
- Vol. 57 (10) , 363-364
- https://doi.org/10.1007/bf02662060
Abstract
The reaction of methyl 4‐hydroxy‐trans‐2‐hexadecenoate [1b] with diiodomethane in the presence of zinc‐copper couple yielded methyl 4‐methoxy‐trans‐2,3‐methylenehexadecanoate [2] in a 70% yield, together with methyl 4‐hydroxy‐trans‐2,3‐methylenehexadecanoate [3] (∼20%). The presence of an allylic hydroxyl group in the α,β‐unsaturated ester increases the yield of the cyclopropanation product. The formation ofo‐methyl ether reveals the dual role of cyclopropanation and etherification by S.S. reagent of a hydroxylated olefinic compound.Keywords
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