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

HRID 1678066Notes

Reaction equation

HRID 1678066 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([C:10]([CH3:12])=[O:11])[CH:7]=[CH:6][C:5]=1[OH:13].I[CH3:15].O>CN(C=O)C>[CH3:3][C:4]1[CH:9]=[C:8]([C:10]([CH3:12])=[O:11])[CH:7]=[CH:6][C:5]=1[O:13][CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 701354'-Hydroxy-3'-methylacetophenone

Product 1

HCID 248061-(4-Methoxy-3-methylphenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (60 percent in mineral oil, 1.44 g, 36 mmol) in anhydrous DMF (30 mL) was added dropwise a solution of 4-hydroxy-3-methylacetophenone (4.5 g, 30 mmol) in dry DMF (20 mL) at 0° C. over a period of 20 minutes. After addition, the mixture was stirred at 0° C. for 30 minutes and iodomethane (2.2 mL, 36 mmol) was added in one portion. The mixture was then stirred at approximately 25° C. overnight. Water was added (10 mL) and the mixture was extracted with ether three times. The combined organic layer was washed with brine, dried over Na2SO4, filtered, concentrated, and dried under vacuum to give crude product as a colorless oil.

Workup

  1. additionAfter addition
  2. stirringThe mixture was then stirred at approximately 25° C. overnight
  3. extractionthe mixture was extracted with ether three times
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried under vacuum
  9. customto give crude product as a colorless oil

Sources & evidence

ORD record
ord-67dfaa63540746cab589fa5beab9761e
Source dataset
uspto-grants-2011_08
Patent number
US08008487B2

Reaction notes

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