3-(Cyanomethyl)benzoic acid

68432-92-8

5689-33-8

Lithium hydroxide (493 mg, 11.7 mmol) was added to a stirred mixed solution of methyl 3-(cyanomethyl)benzoate (1.029 g, 5.87 mmol) in THF (10 ml) and water (0.5 ml) at room temperature. The reaction mixture was stirred continuously at 50 °C overnight. After completion of the reaction, the solvent was removed by evaporation and the residue was partitioned between water and ether. The aqueous phase was extracted three times with ether. Subsequently, the aqueous phase was acidified to acidity with concentrated hydrochloric acid and again extracted three times with ether. All organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 745 mg (79% yield) of 3-cyanomethylbenzoic acid. The product was characterized by 1H NMR (DMSO-D6): δ 13.11 (1H, s), 7.95 (1H, s), 7.90 (1H, d, J = 7.6 Hz), 7.60 (1H, m), 7.53 (1H, t, J = 7.6 Hz), 4.14 (2H, s); MS (ESI) m/z 160 (M-1).