Veratrole → (3,4-dimethoxyphenyl)(4-fluorophenyl)methanone

HRID 1165468Notes

Reaction equation

HRID 1165468 reaction equation
[C:1]1([O:9][CH3:10])[C:2](=[CH:5][CH:6]=[CH:7][CH:8]=1)[O:3][CH3:4].[Cl-].[Al+3].[Cl-].[Cl-].[F:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1.O.Cl>>[CH3:4][O:3][C:2]1[CH:5]=[C:6]([CH:7]=[CH:8][C:1]=1[O:9][CH3:10])[C:20]([C:19]1[CH:23]=[CH:24][C:16]([F:15])=[CH:17][CH:18]=1)=[O:21]

Participants

5

Reactant 4

HCID 7043VeratroleHCID 678794-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 21885828Hydrate;hydrochloride

Product 1

HCID 11076177(3,4-dimethoxyphenyl)(4-fluorophenyl)methanone

Conditions

Temperature
0 °C

Procedure

Veratrole (29.3 g) was added, while stirring, to a mixture of aluminum chloride (34 g) and 4-fluorobenzoyl chloride (35 g) which had been cooled to 0° C., and the resulting mixture allowed to stand for 12 hours at room temperature. It was then boiled for 1 hour. The reaction mixture was then decomposed with water/HCl and extracted with chloroform.

Workup

  1. waitIt was then boiled for 1 hour
  2. extractionextracted with chloroform

Sources & evidence

ORD record
ord-8f01a8641f7e42d4bf8c99dadd660b4f
Source dataset
uspto-grants-1990_03
Patent number
US04910200

Reaction notes

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