Potassium Hydroxide → 3-Cyano-4-hydroxybenzoic acid

Participants

Reaction Steps

Methyl-3-cyano-4-hydroxybenzoate (2.71 g, 15.3 mmol) was dissolved in 50 mL of THF. The solution was chilled in an ice bath, and 2.0M potassium hydroxide (17 mL, 34 mmol) was added dropwise. The resulting mixture was stirred at room temperature overnight. TLC indicated complete reaction. The THF was removed by rotary evaporation. The aqueous residue was acidified with aqueous trifluoroacetic acid and purified by reverse-phase HPLC (C-18, 0.1% TFA in water and acetonitrile). 3-Cyano-4-hydroxybenzoic acid was obtained as a white powder (2.1 g, 84%) after lyophilization.

Provenance & Evidence