Reacción #55287

Ecuación de reacción

phthalic anhydride

N,N-diethyl-m-toluidine

aluminum chloride

chlorobenzene

chlorobenzene

→

2-(2-methyl-4-(diethylamino)benzoyl)benzoic acid

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated (75°-95° C.) during one and one-half hours
2. 2
   Otrothe chlorobenzene layer was separated
3. 3
   workup.DISTILLATIONsteam distilled
4. 4
   workup.ADDITIONAddition of sodium hydroxide solution (10%) to a solution of the residue in dilute sulfuric acid (20%, 250 ml.)

Procedimiento

A mixture of phthalic anhydride (60 g.), N,N-diethyl-m-toluidine (162.8 g.), aluminum chloride (120 g.) and chlorobenzene (360 ml.) was heated (75°-95° C.) during one and one-half hours, then diluted with water (200 ml., then more). More chlorobenzene (200 ml.) was added and the chlorobenzene layer was separated and steam distilled. Addition of sodium hydroxide solution (10%) to a solution of the residue in dilute sulfuric acid (20%, 250 ml.) afforded 2-(2-methyl-4-(diethylamino)benzoyl)benzoic acid (IV: Y2 =CH3, Y'4 =(CH3CH2)2N, Z4 =Z"5 =Z"6 =Z7 =H).

Fuente