Hydrochloric Acid → 3-(4-Chlorosulfonyl-phenyl)-acrylic acid

Participants

Reaction Conditions

Reaction Steps

To neat chlorosulfonic acid (26.5 mL, 0.4 mol) at 18° C. temperature slowly cinnamic acid (7) (7.35 g, 0.05 mol) was added. As the reaction proceeded, hydrogen chloride gas evolved. The reaction mixture was stirred successively at 20° C. for 3 hours and at 42° C. for 3 hours. The dark, viscous syrup was poured into ice water, and the precipitated solid was filtered and washed with water. The title compound was obtained (6.8 g, 55%) as a white solid. 1H NMR (DMSO-d6, HMDSO), δ: 6.55 (1H, d, J=16.0 Hz); 7.58 (1H, d, J=16.0 Hz); 7.65 (4H, s); 8.15 (1H, br s).

Provenance & Evidence