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

HRID 2414433Notes

Reaction equation

HRID 2414433 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 to obtain-the title compound

Sources & evidence

ORD record
ord-0bfec44d58c34080a9cda13fb3f62a41
Source dataset
uspto-grants-2004_11
Patent number
US06812231B2

Reaction notes

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