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

HRID 1860585Notes

Reaction equation

HRID 1860585 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[OH:8].[C:12]([O-])([O-])=O.[K+].[K+].O>CO>[CH3:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[O:8][CH3:12]

Participants

5

Reactant 3

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

Product 1

HCID 248061-(4-Methoxy-3-methylphenyl)ethan-1-oneYield 62.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 1-(3-methyl-4-hydroxylphenyl)ethanone (15.02 g, 100 mmol) in MeOH was added K2CO3 (41.5 g, 300 mmol), and Mel (28.4 g, 200 mmol). The reaction mixture was stirred at room temperature for 2 hours. Another 56.7 g of Mel was added, and the reaction mixture was stirred for an additional 2 hours. Water (50 ml) was added, and the product was extracted with 600 ml of EtOAc. The organic layer was washed with brine (250 ml), and dried with Na2SO4, and the solvent was removed in vacuo to give the title compound (10.2 g, 62%).

Workup

  1. additionAnother 56.7 g of Mel was added
  2. stirringthe reaction mixture was stirred for an additional 2 hours
  3. extractionthe product was extracted with 600 ml of EtOAc
  4. washThe organic layer was washed with brine (250 ml)
  5. dry with materialdried with Na2SO4
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8b0150c7581f49bd837c7da8fe0bced9
Source dataset
uspto-grants-2003_03
Patent number
US06531492B1

Reaction notes

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