Water → 3'-(Methylthio)acetophenone

HRID 1011568Notes

Reaction equation

HRID 1011568 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[C:11](=O)([O-])[O-].[K+].[K+].IC.O>CN(C)C=O>[CH3:11][S:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 47132071-(3-Sulfanylphenyl)ethan-1-one

Product 1

HCID 64321073'-(Methylthio)acetophenoneYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 3′-mercaptoacetophenone (Reference compound No. 4-1, 1.5 g, 9.9 mmol), potassium carbonate (1.6 g, 12 mmol) and iodomethane (740 μL, 12 mmol) in N,N-dimethylformamide was stirred at 50° C. for 75 minutes. Water (50 mL) was added to the reaction mixture, extracted with a mixed solvent (50 mL) which consists of hexane and ethyl acetate (3:1). The organic layer was washed with brine (50 mL), dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title reference compound (1.3 g) as a brown oil (Yield 77%).

Workup

  1. extractionextracted with a mixed solvent (50 mL) which
  2. washThe organic layer was washed with brine (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-65fae991888246918556d355125cce78
Source dataset
uspto-grants-2011_07
Patent number
US07977371B2

Reaction notes

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