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Reactions of dimethyl sulfoxide with sulfonate esters of fatty alcohols. I. Synthesis of higher saturated and unsaturated fatty aldehydes
Author(s) -
Mahadevan V.,
Phillips F.,
Lundberg W. O.
Publication year - 1966
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/bf02531870
Subject(s) - chemistry , dimethyl sulfoxide , organic chemistry , sodium bicarbonate , sulfonate , fatty alcohol , aldehyde , chromatography , sodium , catalysis
Long‐chain saturated fatty aldehydes (C 10 to C 18 ), as well as the C 18 unsaturated aldehydes (oleyl, linoleyl, and linolenyl), were synthesized in good yields by the selective oxidation of the sulfonate esters of the corresponding alcohols with dimethyl sulfoxide in the presence of sodium bicarbonate. Chromatographic procedures for the isolation of the pure aldehydes from the reaction mixtures are described. The purity of the aldehydes was ascertained by thin‐layer chromatography, melting points of their 2,4‐dinitrophenyl hydrazones, infrared spectra and other physical methods.