Carbon Dioxide → 2-Methoxy-4,6-bis(trifluoromethyl)benzoic acid

Participants

Reaction Steps

To a solution of 1-methoxy-3,5-bis(trifluoromethyl)benzene (48, 0.56 g, 2.33 mmol) in anhydrous ether (5 mL) was slowly added n-BuLi (1.6 M solution in hexanes, 3 mL, 4.66 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 h. Dry ice was added into the yellow suspension until the starting material was completely consumed as monitored by TLC. The reaction was quenched with H2O (3 mL) and organic layer was separated. The aqueous layer was acidified with concentrated HCl, and then extracted with Et2O (3×5 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 2-methoxy-4,6-bis(trifluoromethyl)benzoic acid (49, 0.38 g, 50%): 1H NMR (300 MHz, DMSO-d6) δ 13.94 (s, 1H), 7.76 (s, 1H), 3.97 (s, 1H).

Provenance & Evidence