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Improved method of preparation of α‐substituted fatty acids
Author(s) -
Linfield Warner M.,
Barauskas Robert A.,
Smith Frank D.
Publication year - 1982
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02636045
Subject(s) - hexamethylphosphoramide , reagent , chemistry , organic chemistry , solvent , refrigeration , combinatorial chemistry , mechanical engineering , engineering
The previously published methods for the syntheses of α‐substituted fatty acids, as developed by Pfeffer et al. and Konen et al., were improved by using the dimethylamides instead of the free carboxylic acids and changing the solvent system to eliminate hexamethylphosphoramide, a known carcinogen. The improved method cuts the use of metalating agent in half, drastically reduces refrigeration requirements, and permits the preparation of larger batches. A Grignard reagent can be used in place of n ‐butyllithium as metalating agent but gives substantially poorer yields. The syntheses of α‐hydroxylauric acid and α‐butyllauric acid are described.