N,N-Diethylaniline → 2,3,4,5-Tetrachloro-6-[4-(diethylamino)-2-methylbenzoyl]benzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of tetrachlorophthalic anhydride (42.8 g.), N,N-diethylaniline (74 g.), aluminum chloride (60 g.) and chlorobenzene (180 ml.) was heated (to 75° C.) during one and one-half hours, then diluted with ice-water (500 ml.). The chlorobenzene layer was separated and steam distilled. Addition of sodium hydroxide solution (50%) to a solution of the residue in dilute sulfuric acid (50%, 250 ml.) afforded 2-(4-(diethylamino)benzoyl)-3,4,5,6-tetrachlorobenzoic acid (IV: Y2 = H, Y'4 = (CH3CH2)2N, Z4 = Z"5 = Z"6 = Z7 = Cl) (59 g., m.p. 228°-233° C.).

Provenance & Evidence