Acetone → 1-Methoxy-3-(methylsulfonyl)benzene

HRID 885086Notes

Reaction equation

HRID 885086 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](SC)[CH:6]=[CH:7][CH:8]=1.O[O:12][S:13]([O-:15])=O.[K+].[CH3:17]C(C)=O>O>[CH3:17][S:13]([C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1)(=[O:15])=[O:12]

Participants

5

Reactant 3

HCID 180AcetoneHCID 2811823-MethoxythioanisoleHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 2596501-Methoxy-3-(methylsulfonyl)benzeneYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-methoxythioanisole (3.084 g, 20 mmol) in 300 mL acetone was added a solution of oxone (30.74 g, 50 mmol) in 125 mL water, resulting in the formation of a white precipitate. Stirring continued overnight, and the solid was filtered off and washed with acetone. Filtrate was concentrated to remove acetone. Aqueous layer was extracted with EtOAc (2×200 mL) and dried over Na2SO4. The solvent was removed to give 1-methanesulfonyl-3-methoxy benzene (3.68 g, 98%) as oil.

Workup

  1. customresulting in the formation of a white precipitate
  2. filtrationthe solid was filtered off
  3. washwashed with acetone
  4. concentrationFiltrate was concentrated
  5. customto remove acetone
  6. extractionAqueous layer was extracted with EtOAc (2×200 mL)
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-a77d81cc485c4568ba517ff9cedff5b1
Source dataset
uspto-grants-2012_08
Patent number
US08242144B2

Reaction notes

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