반응 #55294

반응 방정식

tetrachlorophthalic anhydride

N,N-diethyl-m-toluidine

aluminum chloride

→

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

수율 77.3%

용매

—

ice water

o-dichlorobenzene

반응 조건

후처리

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

실험 절차

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).

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