Veratrole → Bis(3,4-dimethoxyphenyl)methanone

HRID 849281Notes

Reaction equation

HRID 849281 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:16](O)=[O:17]>O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[O:9][CH3:10])[C:16]([C:15]1[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[C:13]([O:12][CH3:11])[CH:14]=1)=[O:17]

Participants

4

Reactant 2

HCID 7043VeratroleHCID 7121Veratric Acid

Product 1

HCID 223042Bis(3,4-dimethoxyphenyl)methanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Surprisingly, it has been found that when polyphosphoric acid is used as the catalyst, 1,2-dimethoxybenzene (veratrole) can be acylated directly using 3,4-dimethoxybenzoic acid (veratric acid). The advantages of this reaction are the ready availability of the starting materials coupled with a high yield and very simple product isolation. After water has been added, the 3,3',4,4'-tetramethoxybenzophenone can be isolated by simple filtration.

Workup

  1. customa high yield

Sources & evidence

ORD record
ord-c37e516c7dbd4bf5b1de63b648438db3
Source dataset
uspto-grants-2000_01
Patent number
US06011178

Reaction notes

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