N,N-Dimethylaniline → 2-[4-(Dimethylamino)benzoyl]benzoic acid

HRID 839530

Reaction equation

HRID 839530 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH3:12][N:13]([CH3:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClC1C=CC=CC=1>[CH3:12][N:13]([CH3:20])[C:14]1[CH:19]=[CH:18][C:17]([C:4]([C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[C:1]([OH:6])=[O:11])=[O:5])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 6811Phthalic AnhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 889372-[4-(Dimethylamino)benzoyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of phthalic anhydride (30 g.), N,N-dimethylaniline (60.5 g.), aluminum chloride (60 g.) and chlorobenzene (180 g.) was heated (to 75° C.) during one hour, then cooled. Ice (500 ml.) was added, the chlorobenzene layer was separated and the chlorobenzene was steam distilled. Addition of base to a solution of the residue in dilute sulfuric acid afforded 2-(4-(dimethylamino)benzoyl)benzoic acid (IV: Y2 = Z4 = Z"5 = Z"6 = Z7 = H, Y'4 = (CH3)2N).

Workup

  1. temperaturecooled
  2. customthe chlorobenzene layer was separated
  3. distillationdistilled
  4. additionAddition of base to a solution of the residue in dilute sulfuric acid

Sources & evidence

ORD record
ord-f88fec8b9caf4f29924de010ab035256
Source dataset
uspto-grants-1978_06
Patent number
US04096176

Linked notes

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