Methyl iodide → 3-Methoxythioanisole

HRID 724259Notes

Reaction equation

HRID 724259 reaction equation
CI.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([SH:11])[CH:8]=[CH:9][CH:10]=1.[C:12](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([S:11][CH3:12])[CH:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 849893-Methoxybenzenethiol

Product 1

HCID 2811823-MethoxythioanisoleYield 99.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl iodide (14.67 ml, 0.235 mol) was added dropwise to a solution of 3-methoxy-benzenethiol (30 g, 0.214 mol) and potassium carbonate (29.6 g, 0.214 mol) in acetone (400 ml) under nitrogen at 3° C. The reaction was allowed to warm to room temperature and the solvent was removed under reduced pressure. The residue was diluted with water (300 ml) and the aqueous layer was extracted with diethylether (3×200 ml). The combined organic extracts were dried over MgSO4 and the solvent was removed under reduced pressure to give 1-Methoxy-3-methylsulfanyl-benzene (32.87 g) as a pale yellow liquid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionThe residue was diluted with water (300 ml)
  3. extractionthe aqueous layer was extracted with diethylether (3×200 ml)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-964d102472ee430686ec0e088d7065cf
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

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