Potassium Hydroxide → 4-Carbamoyl-2-methylbenzoic acid

Participants

Reaction Steps

To 4-cyano-2-methylbenzoic acid (0.071 g, 0.44 mmol) in 2 ml of t-butanol was added potassium hydroxide (0.13 g, 2.15 mmol). The reaction mixture was refluxed for 30 min and cooled to room temperature. To the reaction mixture was added 10 ml of brine and the reaction mixture was extracted with ethyl acetate (2×15 ml). The water layer was acidified to pH 1-2 with concentrated aqueous hydrochloric acid to give a white precipitate. The solid was collected by filtration, washed several times with water (3×15 ml) and dried in vacuo to provide 4-(aminocarbonyl)-2-methylbenzoic acid (0.038 g, 49% yield). 1H-NMR (400 MHz, DMSO-d6): 13.10 (br s, 1H), 8.07 (s, 1H), 7.87 (d, 1H), 7.78-7.72 (m, 2H), 7.50 (s, 1H), 2.54 (s, 3H).

Provenance & Evidence