N,N-Dimethylaniline → 2-[4-(Dimethylamino)benzoyl]benzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of phthalic anhydride (30 g.), N,N-dimethylaniline (60.5 g.), aluminum chloride (60 g.) and chlorobenzene (180 g.) was heated (to 75° C.) during one hour, then cooled. Ice (500 ml.) was added, the chlorobenzene layer was separated and the chlorobenzene was steam distilled. Addition of base to a solution of the residue in dilute sulfuric acid afforded 2-(4-(dimethylamino)benzoyl)benzoic acid (IV: Y2 = Z4 = Z"5 = Z"6 = Z7 = H, Y'4 = (CH3)2N).

Provenance & Evidence