Veratrole → Methyl 4-(3,4-dimethoxybenzoyl)benzoate

HRID 2187956Notes

Reaction equation

HRID 2187956 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl-].[C:6]([O:17][CH3:18])(=[O:16])[C:7]1[CH:15]=[CH:14][C:10]([C:11]([O-:13])=O)=[CH:9][CH:8]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][CH3:28]>ClCCl>[CH3:19][O:20][C:21]1[CH:26]=[C:25]([CH:24]=[CH:23][C:22]=1[O:27][CH3:28])[C:11]([C:10]1[CH:9]=[CH:8][C:7]([C:6]([O:17][CH3:18])=[O:16])=[CH:15][CH:14]=1)=[O:13]

Participants

5

Reactant 3

HCID 7043VeratroleHCID 6451240Aluminum(III) ChlorideHCID 22493623Monomethyl terephthalate chloride

Product 1

HCID 22645197Methyl 4-(3,4-dimethoxybenzoyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

2.1 g (15.72 mmol) of aluminum chloride, a solution of 2.39 g (12.02 mmol) of monomethyl terephthalate chloride dissolved in 2 ml of dichloromethane and 1.2 ml (9.25 mmol) of 1,2-dimethoxybenzene dissolved in 2 ml of dichloromethane were added to 10 ml of dichloromethane, and they were stirred overnight. The reaction solution was poured into 5 g of 1 N hydrochloric acid/ice. After the treatment with chloromethane as the extraction solvent in an ordinary manner, the solvent was evaporated, and the obtained residue was washed with ethyl acetate and dichloromethane to obtain the title compound.

Workup

  1. customAfter the treatment with chloromethane as the extraction solvent in an ordinary manner, the solvent was evaporated
  2. washthe obtained residue was washed with ethyl acetate and dichloromethane

Sources & evidence

ORD record
ord-55990dd6ae334c3eaf48594d903efc95
Source dataset
uspto-grants-2002_06
Patent number
US06410538B2

Reaction notes

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