Functional polymers. XLVII. Synthesis of various derivatives of ω‐alkenoates

A number of derivatives of ω‐alkenoates were synthesized in preparation for the synthesis of functional polymers based on α‐olefins. For the preparation of most of the methyl esters, the regular esterification of ω‐alkenoic acids, specifically 10‐undecenoic acid with methanol and sulfuric acid as the catalyst, was most effective. For the preparation of thetert‐butyl‐ and 2‐ethylhexyl esters of 10‐undecenoic acid, the acid chloride route was found to be most convenient, whereas for the preparation of the corresponding esters of 5‐hexenoic acid, our method of choice was the synthesis via the imidazolyl derivative of the acid. 2,2,2‐Trifluoroethyl 10‐undecenoate and the 2,2‐dimethyloxazolidine derivative of 10‐undecenoic acid were prepared from the acid and 2,2,2‐trifluoroethanol or 2‐amino‐2‐methyl‐propanol withp‐toluene sulfonic acid as the catalyst. Esters of phenol, 2,6‐dimethylphenol, and 2,6‐diphenylphenol were synthesized from 3‐butenoic and 10‐undecenoic acid with trifluoroacetic anhydride.