Methanol → 4-Chloro-2-(trifluoromethyl)phenylacetic acid methyl ester

Participants

Reaction Steps

Thionyl chloride (9.5 mL) was added dropwise to a solution of 4-chloro-2-(trifluoromethyl)phenylacetic acid (CAS #601513-31-9, 10.5 g) in methanol (50 mL) under ice-cooling. Then, the reaction solution was heated under reflux for three hours. The reaction solution was concentrated under reduced pressure. A saturated sodium bicarbonate solution and ethyl acetate were added to the resulting residue, and the organic layer was separated. The resulting organic layer was sequentially washed with a saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 10.96 g of the title compound. 1H-NMR (CDCl3) δ (ppm): 3.71 (s, 3H), 3.80 (s, 2H), 7.35 (d, J=8.4 Hz, 1H), 7.50 (dd, J=8.4, 2.0 Hz, 1H), 7.65 (d, J=2.0 Hz, 1H).

Provenance & Evidence