Methyl iodide → 3-Methylthio-4-methoxyphenylacetone

HRID 1614740Notes

Reaction equation

HRID 1614740 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:14](=O)([O-])[O-].[K+].[K+].CI.C(C(C)=O)C>C(OCC)(=O)C>[CH3:14][S:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 131788863-Mercapto-4-methoxyphenylacetone

Product 1

HCID 131788873-Methylthio-4-methoxyphenylacetoneYield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 10 g of 3-mercapto-4-methoxyphenylacetone, 9 g of anhydrous potassium carbonate, 42 g of methyl iodine, and 50 ml of methyl ethyl ketone was stirred under refluxing for 20 hours, and after cooling, the reaction mixture was filtered. The filtrate obtained was, then, evaporated to dryness. The residue formed was dissolved in ethyl acetate and after washing the solution obtained with water, ethyl acetate was distilled off and the crude crystals obtained were recrystallized from a mixture of n-hexane and ether to provide 9 g of 3-methylthio-4-methoxyphenylacetone having a melting point of 74°-75° C.

Workup

  1. temperatureunder refluxing for 20 hours
  2. temperatureafter cooling
  3. filtrationthe reaction mixture was filtered
  4. customThe filtrate obtained
  5. customevaporated to dryness
  6. customThe residue formed
  7. washafter washing the solution
  8. customobtained with water, ethyl acetate
  9. distillationwas distilled off
  10. customthe crude crystals obtained
  11. customwere recrystallized from a mixture of n-hexane and ether

Sources & evidence

ORD record
ord-5e4adef6c84c44b4bbc08ecf622615aa
Source dataset
uspto-grants-1993_03
Patent number
US05198587

Reaction notes

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