Methanesulfonic acid catalyzed additions to oleic acid and cyclohexene. III. Addition of acids and substituted phenols

Abstract

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.

Use of Sonication for the Coupling of Sterically Hindered Substrates in the Phenolic Mitsunobu Reaction

“…The following aryl ethers from Table 1 have been reported in the literature: Entry 1, 12 Entry 4, 13 Entry 5, 14 Entry 6, 15 and Entry 7. 16 Characterization data for new compounds are given below.…”

Addition of aromatic compounds to oleic acid catalyzed by heterogeneous acid catalysts

“…The addition of aromatic compounds to oleic acid has been studied using various types of Lewis and Bronsted acids as catalysts (1,2). Eisner et al (3)(4)(5) reported that methanesulfonic acid was the preferred acid catalyst for the addition reaction of aromatic compounds to oleic acid because this acid gave not only good yields of addition products, but products with less color. Recently, Nakano et al (6) identified all of the reaction products formed when aromatic compounds are reacted with oleic acid in the presence of methanesulfonic acid and proposed a reaction pathway to account for the products identified.…”

“…As early as 1960, Mangio (1)came to some useful conclusions on the presence of animal and other vegetable fats in olive oil. The application of reversed-phase thin layer (TLC) and paper chromatography revealed distinct differences in the chromatograms of pure olive oil and of samples adulterated with vegetable oil, which can be used for detecting the presence of low concentrations (10%) of vegetable oils in olive oil (2,3,4). Galanos et al (5,6) have shown that differences in the triglyceride composition of vegetable oils can be used for detecting adulteration of olive oil.…”