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Methanesulfonic acid catalyzed additions to oleic acid and cyclohexene. III. Addition of acids and substituted phenols
Author(s) -
Eisner Abner,
Perlstein Theodore,
Ault W. C.
Publication year - 1963
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/bf02822475
Subject(s) - methanesulfonic acid , chemistry , benzoic acid , saponification , catalysis , phenols , organic chemistry , yield (engineering) , resorcinol , oleic acid , solvent , nucleophile , cyclohexene , medicinal chemistry , biochemistry , materials science , metallurgy
Benzoic acid adds to oleic acid in methanesulfonic acid as catalyst‐solvent to form an addition product in 30% yield. Saponification studies on the product reveal that the addition is made via the carboxyl group and no rearrangement of the initial product takes place. A number of substituted benzoic acids were also tried but the yield of addition product was nil. Data are included for the experiments with a number of phenols not previously reported. These include: o‐chlorophenol,2,6‐di‐tert.‐butylphenol, 2,4,6‐trichlorophenol, resorcinol, 5‐n‐pentadecylresorcinol, hydroquinone, methyl salicylate, and 3‐n‐pentadecylphenol. Good yields of addition products of cyclohexene are obtained using methanesulfonic acid as catalyst‐solvent and the same nucleophiles employed previously.