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

HRID 378528Notes

Reaction equation

HRID 378528 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].IC.[C:14]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:11][C:3]1[CH:4]=[C:5]([C:8]([CH3:9])=[O:10])[CH:6]=[CH:7][C:2]=1[O:1][CH3:14]

Participants

5

Reactant 3

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

Product 1

HCID 248061-(4-Methoxy-3-methylphenyl)ethan-1-oneYield 82.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4'-hydroxy-3'-methylacetophenone (5.0 g, 33.3 mmol), iodomethane (5.7 g, 40.0 mmol), K2CO3 (granular, anhydrous) (23.0 g, 167 mmol), and acetone (250 mL) was refluxed for 3 hours. The reaction mixture was then cooled to room temperature, filtered to remove the inorganic salts, and evaporated under vacuum. The crude product was dissolved in ether (100 mL) and washed with H2O (2×20 mL). The organic layer was dried (Na2SO4) and evaporated to yield 4.5 g, 82.4% yield. The ketone was used in the following reaction without further purification.

Workup

  1. temperaturewas refluxed for 3 hours
  2. filtrationfiltered
  3. customto remove the inorganic salts
  4. customevaporated under vacuum
  5. dissolutionThe crude product was dissolved in ether (100 mL)
  6. washwashed with H2O (2×20 mL)
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. customevaporated
  9. customto yield 4.5 g, 82.4% yield

Sources & evidence

ORD record
ord-3a472d30ff4e4ea9a70f834bc5a791d0
Source dataset
uspto-grants-2000_02
Patent number
US06031003

Reaction notes

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