Water → 2-(2-Methylanilino)-benzene-1,4-dicarboxylic acid

Participants

Reaction Conditions

Reaction Steps

Bromoterephthalic acid (12.2 g), ortho-toluidine (10.7 ml), anhydrous K2CO3 (13.8 g), catalytic Cu powder (0.2 g) in 2-ethoxy-ethanol (17.5 ml) were stirred together while heating under reflux conditions in an oil bath at 150° C. After 6 hours, water (200 ml) was added and, when all salts had dissolved, the solution was clarified and crude product precipitated by acidification to pH 2. The collected diacid was well washed with boiling water then recrystallised from 50% ethanol, pure product being obtained as yellow needles of mp 318° C. (dec).

Provenance & Evidence