Lithium Hydroxide → 3-cyano-5-methoxybenzoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 3-cyano-5-methoxy-benzoic acid methyl ester (3.4 g, 18.7 mmol) in THF (45 mL) was treated with 0.5 N lithium hydroxide (45 mL, 22.4 mmol). The reaction was stirred at 75° C. for 2 h and then the solvent was removed in vacuo. The residue was dissolved in a small amount of water and then acidified (pH 2) by the addition of 1 N HCl. Ethyl acetate was used to extract the precipitate, which was then washed with brine and dried over anhydrous sodium sulfate. After removal of solvent in vacuo, 2.5 g (77%) of 3-cyano-5-methoxybenzoic acid was isolated as a white solid. 1H NMR (DMSO), δ(ppm): 7.86 (s, 1H), 7.71 (m, 2H), 3.87 (s, 3H).

Provenance & Evidence