Phthalic Anhydride → 2-[4-(Diethylamino)-2-hydroxybenzoyl]benzoic acid

HRID 565077Notes

Reaction equation

HRID 565077 reaction equation
[CH2:1]([N:3]([CH2:11][CH3:12])[C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)[CH3:2].[C:13]1(=[O:23])[O:18][C:16](=[O:17])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12>C1(C)C=CC=CC=1>[C:16]([C:15]1[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=1[C:13]([C:7]1[CH:8]=[CH:9][C:4]([N:3]([CH2:1][CH3:2])[CH2:11][CH3:12])=[CH:5][C:6]=1[OH:10])=[O:23])([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 70623-(Diethylamino)phenol

Product 1

HCID 798782-[4-(Diethylamino)-2-hydroxybenzoyl]benzoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(2′-Carboxybenzoyl)-5-diethylaminophenol was prepared as follows. A mixture of m-diethylaminophenol (1 mole) and phthalic anhydride (1.2 moles) was refluxed in toluene (2.0 L) for about 16 hours, cooled, and the resulting solid filtered, washed with toluene and dried to give 2-(2′-carboxybenzoyl)-5-diethylaminophenol in 70% yield.

Workup

  1. custom2-(2′-Carboxybenzoyl)-5-diethylaminophenol was prepared
  2. temperaturecooled
  3. filtrationthe resulting solid filtered
  4. washwashed with toluene
  5. customdried

Sources & evidence

ORD record
ord-6101d14e85e44ff5aac0ecc59b3cd271
Source dataset
uspto-grants-2001_01
Patent number
US06169185A

Reaction notes

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