反応 #55294

反応方程式

tetrachlorophthalic anhydride

N,N-diethyl-m-toluidine

aluminum chloride

→

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

収率 77.3%

溶媒

—

ice water

o-dichlorobenzene

反応条件

後処理

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

実験手順

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).

出典