Reactions of dimethyl sulfoxide with sulfonate esters of fatty alcohols. I. Synthesis of higher saturated and unsaturated fatty aldehydes
- 30 April 1966
- Vol. 1 (3) , 183-187
- https://doi.org/10.1007/bf02531870
Abstract
Long‐chain saturated fatty aldehydes (C10 to C18), as well as the C18 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.This publication has 20 references indexed in Scilit:
- Dimethyl Sulfoxide-Acid Anhydride Mixtures. New Reagents for Oxidation of Alcohols1Journal of the American Chemical Society, 1965
- The conversion of alcohols to aldehydes and ketones: A superior methodTetrahedron Letters, 1964
- Conversion of oleyl and elaidyl tosylates to aldehydesJournal of Oil & Fat Industries, 1964
- The preparation of polyunsaturated aliphatic aldehydesvia the acyloin condensationJournal of Oil & Fat Industries, 1960
- The Preparation of Olefins from Arylsulfonate Esters of Alcohols1Journal of the American Chemical Society, 1959
- A NEW AND SELECTIVE METHOD OF OXIDATION. THE CONVERSION OF ALKYL HALIDES AND ALKYL TOSYLATES TO ALDEHYDESJournal of the American Chemical Society, 1959
- Oxidations by manganese dioxide in neutral mediaQuarterly Reviews, Chemical Society, 1959
- Sulfoxides as nucleophilesTetrahedron, 1958
- Synthesis of Several Phosphorylated Derivatives of Dihydrosphingosine1Journal of the American Chemical Society, 1957
- A New Preparation of 2,4-DinitrophenylhydrazonesJournal of the American Chemical Society, 1951