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Alkylation of carboxylic acids at the 2-position with conjugated olefins such as isoprene, butadiene, myrcene, and styrene were carried out. For example, 2, 2, 5-trimethyl-4-hexenoic acid (3) was obtained in 66% yield from the reaction of isobutyric acid (1) and isoprene (2) using sodium naphthalenide in the presence of N, N, N', N'-tetramethylethylenediamine. Similarly, from isobutyric acid (1) and styrene (5), 2, 2-dimethyl-4-phenylbutyric acid (6) was obtained in 57% yield. Furthermore, conversion of these carboxylic acids to alcohols, aldehydes, and lactones were examined.

Reaction of Carboxylic Acids with Conjugated Olefins, Using Sodium Naphthalenide in the Presence of N, N, N', N'-Tetramethylethylenediamine