Potassium Hydroxide → 4-(Difluoromethyl)benzoic acid

Participants

Reaction Steps

Dissolve methyl 4-(difluoromethyl)benzoate (2.855 g, 15.336 mmol) in MeOH (30 mL). Add potassium hydroxide (8.41 mL 2 equivalents, 30.7 mmol), and stir the mixture for 16 hours. Concentrate the reaction mixture under reduced pressure, and add EtOAc (100 mL) and 1 N HCl (50 mL). Stir for 30 minutes. Separate the layers. Dry the organics over Na2SO4; filter; collect the filtrate; and concentrate the filtrate under reduced pressure to give the titled compound as a white solid (2.541 g, 96% yield). 1H NMR (399.83 MHz, d6-DMSO) δ 13.29-13.28 (m, 1H), 8.04 (d, J=7.8 Hz, 2H), 7.67 (d, J=8.0 Hz, 2H), 7.24-6.97 (t, J=55.6, 1H).

Provenance & Evidence