Phthalic Anhydride → 2-(4-(Diethylamino)-2-methylbenzoyl)benzoic acid

HRID 839341Notes

Reaction equation

HRID 839341 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.[CH2:12]([N:14]([CH2:22][CH3:23])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=1)[CH3:13].[Cl-].[Al+3].[Cl-].[Cl-].ClC1C=CC=CC=1>O>[CH3:21][C:17]1[CH:16]=[C:15]([N:14]([CH2:12][CH3:13])[CH2:22][CH3:23])[CH:20]=[CH:19][C:18]=1[C:4]([C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[C:1]([OH:6])=[O:11])=[O:5]

Participants

6

Reactant 4

HCID 6811Phthalic AnhydrideHCID 7964Chlorobenzene2×HCID 66679N,N-diethyl-m-toluidineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1043352-(4-(Diethylamino)-2-methylbenzoyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of phthalic anhydride (60 g.), N,N-diethyl-m-toluidine (162.8 g.), aluminum chloride (120 g.) and chlorobenzene (360 ml.) was heated (75°-95° C.) during one and one-half hours, then diluted with water (200 ml., then more). More chlorobenzene (200 ml.) was added and the chlorobenzene layer was separated and steam distilled. Addition of sodium hydroxide solution (10% to a solution of the residue in dilute sulfuric acid (20%, 250 ml.) afforded 2-(2-methyl-4-(diethylamino)benzoyl)benzoic acid (IV: Y2 = CH3, Y'4 = (CH3CH2)2N, Z4 = Z"5 = Z"6 = Z7 = H).

Workup

  1. temperaturewas heated (75°-95° C.) during one and one-half hours
  2. customthe chlorobenzene layer was separated
  3. distillationsteam distilled
  4. additionAddition of sodium hydroxide solution (10% to a solution of the residue in dilute sulfuric acid (20%, 250 ml.)

Sources & evidence

ORD record
ord-2a22abe0403c405e98bb99f7de727b7f
Source dataset
uspto-grants-1978_06
Patent number
US04094877

Reaction notes

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