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

HRID 839348Notes

Reaction equation

HRID 839348 reaction equation
[Cl:1][C:2]1[C:3]([Cl:15])=[C:4]([Cl:14])[C:5]([Cl:13])=[C:6]2[C:11](=[O:12])[O:10][C:8](=[O:9])[C:7]=12.[CH2:16]([N:18]([CH2:26][CH3:27])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=1)[CH3:17].[Cl-].[Al+3].[Cl-].[Cl-]>ClC1C=CC=CC=1Cl>[CH3:25][C:21]1[CH:20]=[C:19]([N:18]([CH2:16][CH3:17])[CH2:26][CH3:27])[CH:24]=[CH:23][C:22]=1[C:11]([C:6]1[C:5]([Cl:13])=[C:4]([Cl:14])[C:3]([Cl:15])=[C:2]([Cl:1])[C:7]=1[C:8]([OH:10])=[O:9])=[O:12]

Participants

5

Reactant 3

HCID 8326Tetrachlorophthalic anhydrideHCID 66679N,N-diethyl-m-toluidineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1043362,3,4,5-Tetrachloro-6-[4-(diethylamino)-2-methylbenzoyl]benzoic acidYield 77.3%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

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).

Workup

  1. temperaturewas heated (75°-95° C.) during one to two hours
  2. customThe o-dichlorobenzene layer was separated
  3. distillationsteam distilled
  4. temperatureThe residue was heated with dilute sulfuric acid
  5. additionThe mixture was poured onto ice
  6. temperatureThe resulting oil was heated in concentrated sulfuric acid
  7. customDilution with water and purification of the product with toluene and hexane

Sources & evidence

ORD record
ord-0fdcc41f71204f5d9223ddb81e1ab344
Source dataset
uspto-grants-1978_06
Patent number
US04094877

Reaction notes

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