Water → 1-(4-Methoxy-3-methylphenyl)ethan-1-one

HRID 2406055Notes

Reaction equation

HRID 2406055 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[CH3:11].[C:12](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[CH3:12][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 701354'-Hydroxy-3'-methylacetophenone

Product 1

HCID 248061-(4-Methoxy-3-methylphenyl)ethan-1-oneYield 100.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4′-hydroxy-3′-methylacetophenone (25.0 g) in N,N-dimethylformamide (120 ml) were added potassium carbonate (69.1 g) and methyl iodide (11.4 ml) under ice-cooling, and the mixture was stirred for 2 hr under ice-cooling and further at room temperature for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (27.5 g) as a yellow oil.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6bd4da24838240bd996cae4047922b8a
Source dataset
uspto-grants-2014_08
Patent number
US08809304B2

Reaction notes

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