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A simple and efficient synthesis of fatty thioacids
Author(s) -
Shin HyeonCheol,
Quinn Daniel M.
Publication year - 1993
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02536365
Subject(s) - yield (engineering) , fatty acid , chemistry , organic chemistry , staring , fatty alcohol , one step , chemical engineering , materials science , communication , sociology , engineering , metallurgy
Abstract A rapid and high‐yielding two‐step synthesis of fatty thioacids from readily available staring materials has been devised. In the first step, an acid chloride is reacted with thioacetic acid at room temperature to produce a mixed thioanhydride, which in the second step is nucleophilically deacetylated with propylamine or butylamine at 5°C. Each step is complete in five minutes and proceeds in quantitative yield. The versatility of the procedure is demonstrated by the synthesis of fatty thioacids from six to sixteen carbons in length.