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

HRID 839532Notes

Reaction equation

HRID 839532 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>[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

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

In a manner similar to that of part A of Example 1 condensation of phthalic anhydride (60 g.) and N,N-diethyl-m-toluidine (162.8 g.) in contact with aluminum chloride (120 g.) and with chlorobenzene (360 ml.) as diluent afforded 2-(2-methyl-4-(diethylamino)benzoyl)benzoic acid (IV: Y2 = CH3, Y'4 = (CH3CH2)2N, Z4 = Z"5 = Z"6 = Z7 = H).

Sources & evidence

ORD record
ord-8b88cd6b8b8c497d9dabc9ab9cfd60a7
Source dataset
uspto-grants-1978_06
Patent number
US04096176

Reaction notes

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