Reaktion #55294

Reaktionsgleichung

tetrachlorophthalic anhydride

N,N-diethyl-m-toluidine

aluminum chloride

→

2-(2-methyl-4-(diethylamino)benzoyl)-3,4,5,6-tetrachlorobenzoic acid

Ausbeute 77.3%

Lösungsmittel

—

ice water

o-dichlorobenzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated (75°-95° C.) during one to two hours
2. 2
   SonstigeThe o-dichlorobenzene layer was separated
3. 3
   workup.DISTILLATIONsteam distilled
4. 4
   TemperaturThe residue was heated with dilute sulfuric acid
5. 5
   workup.ADDITIONThe mixture was poured onto ice
6. 6
   TemperaturThe resulting oil was heated in concentrated sulfuric acid
7. 7
   SonstigeDilution with water and purification of the product with toluene and hexane

Vorschrift

A mixture of tetrachlorophthalic anhydride (21.4 g.), N,N-diethyl-m-toluidine (41 g.), aluminum chloride (30 g.) and o-dichlorobenzene (90 ml.) was heated (75°-95° C.) during one to two hours, then diluted with ice-water. The o-dichlorobenzene layer was separated and steam distilled. The residue was heated with dilute sulfuric acid. The mixture was poured onto ice and made alkaline. The resulting oil was heated in concentrated sulfuric acid. Dilution with water and purification of the product with toluene and hexane afforded 2-(2-methyl-4-(diethylamino)benzoyl)-3,4,5,6-tetrachlorobenzoic acid (IV: Y2 =CH3, Y'4 =(CH3CH2)2N, Z4 =Z"5 =Z"6 =Z7 =Cl) (26 g., m.p. 117° C. with sublimation).

Quelle