Sodium Hydroxide → trans-4-Cyanocyclohexanecarboxylic acid

Participants

Reaction Steps

To the solution of methyl 4-cyanocyclohexylcarboxylate (470 mg, 2.81 mole) prepared according to the method described in J. Am. Chem. Soc., 82, 2547 (1960) in methanol (5 ml) was added 1N sodium hydroxide (2.8 ml) under ice-cooling, and the mixture was stirred overnight during which the temperature of the mixture was left rising up to room temperature. After the reaction mixture was concentrated, water was added. The resulting mixture was washed with ether and acidified with 5N hydrochloric acid. After extracted thrice with chloroform, the mixture was dried with anhydrous magnesium sulfate. After the inorganic salt was removed by filtration, the filtrate was concentrated under reduced pressure to give 362 mg of the title compound as a colorless crystal (yield, 84%).

Provenance & Evidence