Lithium Hydroxide → 3-(1-Cyanocyclopropyl)benzoic acid

Participants

Reaction Steps

A solution of 33 (1.56 g, 7.75 mmol) in 25 mL of THF/MeOH/H2O (3/1/1) was added lithium hydroxide (613 mg, 25.6 mmol) in water (5 mL). The mixture was stirred overnight at rt. Concentrated in vacuo and the resulting solution was acidified with 1N HCl (until pH=1). The resulting precipitate was collected and washed with water and dried to give 3-(1-cyanocyclopropyl)benzoic acid 34 (1.19 g, 82%). NMR (400 MHz, CDCl3) 1.49 (m, 2H), 1.81 (m, 2H), 7.50 (t, J=7.8 Hz, 1H), 7.67 (m, 1H), 7.94 (m, 1H), 8.05 (m, 1H).

Provenance & Evidence