Hydrochloric Acid → HCID 131719366, compound

Participants

Reaction Steps

To a solution of 70 percent epoxysuccinic acid, disodium salt (6.573 g, 26 14 mmol) in 25 mL water was added a filtered solution of 4-aminothiophenol (3.251 g, 25.97 mmol) in aq NaOH (28 mmol in 20 mL of water) via polyethylene cannula under nitrogen with stirring. After 22 hours, the cloudy reaction mixture was washed with 30 mL of ether and then acidified to pH 3 with 6M HCl, (13.3 mL, 79.8 mmol) producing a white solid precipitate. The solid was washed with 20 mL of water and dried (70° C., 0.05 mm Hg vacuum) to afford 3.364 g, (50 percent of theoretical) of 2-[4'-(amino)thiophenoxy]-3-hydroxymaleic acid; 1H NMR (DMSO-d6, d) 8.1 (2H, br), 7.13 (2H, d, J=8.3 Hz), 6.48 (2H, d, J=8.3 Hz), 4.05 (2H, d, J=7.6 Hz), 3.47 (2H, d, J=7.6 Hz); 13C NMR (DMSO-d6, d) 173.1, 171.3, 149.4, 136.0, 116.2, 114.1, 70.4, 56.0; IR (Nujol mull, cm-1) 3410 (br, m), 1710 (br, m).

Provenance & Evidence