Anisole → Benzoic acid, 4-(4-methoxybenzoyl)-, methyl ester

HRID 747780Notes

Reaction equation

HRID 747780 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7](=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([C:14](Cl)=[O:15])=[CH:10][CH:9]=1.[C:18]1([O:24][CH3:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClCCl>[CH3:25][O:24][C:18]1[CH:23]=[CH:22][C:21]([C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:7]([O:6][CH3:5])=[O:17])=[CH:9][CH:10]=2)=[O:15])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 257913Benzoic acid, 4-(4-methoxybenzoyl)-, methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.1 g (16 mmol) of aluminum chloride and 2.4 g (12 mmol) of 4-chlorocarbonyl benzoic acid monomethyl ester were stirred in 15 ml of dichloromethane under stirring under cooling with ice. 1.0 g (9.3 mmol) of anisole was added to the resultant mixture. Two hours after, the temperature was elevated to room temperature, and the mixture was stirred overnight. After the treatment with dichloromethane as the extractant in an ordinary manner, the solvent was distilled off. The residue was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. temperatureunder cooling with ice
  2. customTwo hours
  3. customwas elevated to room temperature
  4. stirringthe mixture was stirred overnight
  5. distillationAfter the treatment with dichloromethane as the extractant in an ordinary manner, the solvent was distilled off
  6. customThe residue was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-79367f6aba3647019b7e0979400b4557
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

Loading…