Methyl iodide → 1-(4-Methoxy-3-methylphenyl)ethan-1-one

HRID 628510Notes

Reaction equation

HRID 628510 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].CI.[C:14](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:14][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

5

Reactant 3

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

Product 1

HCID 248061-(4-Methoxy-3-methylphenyl)ethan-1-oneYield 96.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1 (4 hydroxy-3-methylphenyl)-ethanone 5.0 g, methyl iodide 5.70 g, potassium carbonate 20.0 g and acetone 200 ml was stirred with heating under reflux for six hours. The reaction mixture was filtered and was extracted with ethyl acetate. The organic layer was washed with water and was dried over anhydrous magnesium sulfate, and was then concentrated under reduced pressure to give 1-(4-methoxy-3-methylphenyl)-ethanone 5.3 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for six hours
  3. filtrationThe reaction mixture was filtered
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-037b687dc87a4f01959dabf9660d5887
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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