Potassium hydroxide methanol → HCID 67403735, compound

Participants

Reaction Steps

Methyl 4-cyano-2-methyl-3-(methyloxy)benzoate (150 mg, 0.73 mmol) in a solution of 35% aqueous potassium hydroxide:methanol (1:3, 4 mL) was stirred at 60° C. for 1 hour. The mixture was cooled to room temperature, and the methanol was removed by rotary evaporation. Water (4 mL) was added to the mixture and the pH was adjusted to 2 using concentrated aqueous hydrochloric acid. The precipitate which formed was collected by filtration and was washed with water, then hexanes to afford 86 mg, 0.45 mmol (62%) of 4-cyano-2-methyl-3-(methyloxy)benzoic acid. 1H NMR (400 MHz, d6-DMSO): 7.72 (d, 1H), 7.60 (d, 1H), 3.90 (s, 3H), 2.40 (s, 3H). MS (EI) for C10H9NO3: 190 (M−H).

Provenance & Evidence