Hydrochloric Acid → 7-Phenylhept-5-ynoic acid

Participants

Reaction Conditions

Reaction Steps

Hex-5-ynoic acid (0.1 mole) is added to a tetrahydrofuran solution of ethylmagnesium bromide (0.2 mole) maintained at 5° C. When the addition is complete, the solution is warmed to room temperature and CuCN (0.5 g) is added with stirring. After 20 minutes, a solution of benzylbromide (0.05 mole) in tetrahydrofuran is added dropwise over a one-half hour period. The reaction is maintained at room temperature until thin layer chromatography shows completion and then poured onto 1 N hydrochloric acid. This mixture is then extracted with ethyl ether and the ether layer separated. Removal of the ether gives a residue which is distilled under reduced pressure to afford the title product, 7-phenylhept-5-ynoic acid.

Provenance & Evidence