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

HRID 2294653Notes

Reaction equation

HRID 2294653 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-1eebc6c4278d47e2847bce53e3ef62d6
Source dataset
uspto-grants-1997_11
Patent number
US05688938

Reaction notes

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