Sodium Carbonate → 2,3-Dichloro-α-cyanobenzenepropanoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-cyano-3-(2,3-dichlorophenyl)propanoate (1.02 g, 3.63 mmol) in methanol/water (15 mL/15 mL) was added sodium carbonate (1.54 g, 14.5 mmol). The mixture was stirred at 65° C. overnight. After cooled to room temperature, the mixture was concentrated under vacuo to remove MeOH, the resulting mixture was then acidified with 4 N hydrochloric acid. This solution was extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with water and brine, dried over sodium sulphate, concentrated under reduced pressure to give the titled product (0.87 g, 98%) as a white solid; LC/MS: MS (ES+) m/e 244 (MH+); 1H NMR (300 MHz, CDCl3) δ ppm 3.21 (dd, J=10.2, 13.8 Hz, 1H), 3.59 (dd, J=5.4, 13.8 Hz, 1H), 3.87-3.92 (dd, J=5.4, 10.2 Hz, 1H), 4.74 (s, br, 1H), 7.18-7.32 (m, 2H), 7.44 (dd, J=1.8, 7.8 Hz, 1H).

Provenance & Evidence