Veratrole → Bis(3,4-dimethoxyphenyl)methanone

HRID 849285Notes

Reaction equation

N[C:2]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[CH:16][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1)=[O:5].COC1C=CC=CC=1OC.COC1C=C(C=CC=1OC)C(O)=O>>[CH3:15][O:14][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=1[O:12][CH3:13])[C:4]([C:3]1[CH:2]=[CH:19][C:18]([O:20][CH3:21])=[C:17]([O:22][CH3:23])[CH:16]=1)=[O:5]

Participants

Reactant 3

HCID 7043Veratrole

HCID 7121Veratric Acid

HCID 99269672-Amino-4,5,3',4'-tetramethoxybenzophenone

Product 1

HCID 223042Bis(3,4-dimethoxyphenyl)methanone

Procedure

A process for the preparation of 2-amino-4,5,3',4'-tetramethoxybenzophenone of formula: comprising, in a first stage, acylating 1,2-dimethoxybenzene using 3,4-dimethoxybenzoic acid in the presence of polyphosphoric acid to provide 3,3',4,4'-tetramethoxybenzophenone of formula: ##STR10## in a second stage, nitrating the 3,3',4,4'-tetramethoxybenzophenone of formula II using nitric acid in the presence of acetic acid to 2-nitro-4,5,3',4'-tetramethoxybenzophenone of formula: ##STR11## and, in a third stage, reducing the 2-nitro-4,5,3',4'-tetramethoxybenzophenone of formula III to the 2-amino-4,5,3',4'-tetramethoxybenzophenone of formula I.

Sources & evidence

ORD record: ord-f64350f2bf594435842154f3ae076378
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06011178

Reaction notes

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