Water → 1-(2,4-Dimethoxyphenyl)ethanone

HRID 462139

Reaction equation

HRID 462139 reaction equation
[CH3:1][C:2]([C:4]1[CH:12]=[CH:11][C:9]([OH:10])=[C:6](OC)[CH:5]=1)=[O:3].S(OC)([O:16][CH3:17])(=O)=O.[C:20](=O)([O-])[O-].[Na+].[Na+].O>C1C=CC=CC=1>[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:9]([O:10][CH3:20])=[CH:11][C:12]=1[O:16][CH3:17])=[O:3]

Participants

6

Reactant 4

HCID 962Water2×HCID 2214AcetovanilloneHCID 6497Dimethyl SulfateHCID 10340Sodium Carbonate

Product 1

HCID 700161-(2,4-Dimethoxyphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

10 g of acetovanillone (0.06 mol) was methylated with 10.25 g of dimethyl sulfate (0.083 mol) and 8.0 g of sodium carbonate. The reaction mixture was stirred at 80°-90° C for 2 hr. while 6 ml of water were added dropwise over the last 1.2 hr. Addition of water, acidification, and extraction with benzene produced a nearly quantitative yield of 2,4-dimethoxyacetophenone containing less than 0.3% acetovanillone.

Sources & evidence

ORD record
ord-53ad9b6fae294a6cbcb7f7bd0053547c
Source dataset
uspto-grants-1977_12
Patent number
US04065504

Linked notes

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