Sodium Sulfite → 2-Methoxy-6-methylsulfonylnaphthalene

HRID 1738301Notes

Reaction equation

HRID 1738301 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8](SC)[CH:9]=2)[CH:4]=1.Cl[C:16]1C=C(C=CC=1)C(OO)=O.[S:26]([O-:29])([O-])=[O:27].[Na+].[Na+]>C(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([S:26]([CH3:16])(=[O:29])=[O:27])[CH:9]=2)[CH:4]=1

Participants

6

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 4913387HCID 4913387, compound

Product 1

HCID 154346222-Methoxy-6-methylsulfonylnaphthaleneYield 93.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methoxy-6-methylthionaphthalene (1.0 g, 4.9 mmol), [prepared as described in Step 1], in methylene chloride (50 ml) was added 3-chloroperoxybenzoic acid (3.5 g, 10.3 mmol, 50-60%) portionwise. After 0.5 h, the reaction mixture was cooled in an ice bath, sodium sulfite (0.53 g, 4.2 mmol) was added and the stirring was continued for another 20 minutes. The reaction mixture was then poured in water and the organic layer was separated and dried over sodium sulfate. The solvent was removed in vacuo and the crude product was purified by flash chromatography (gradient elution 30-50% ethyl acetate/hexanes) to give 930 mg of 2-methoxy-6-methylsulfonylnaphthalene (80% yield).

Workup

  1. temperaturethe reaction mixture was cooled in an ice bath
  2. waitthe stirring was continued for another 20 minutes
  3. customthe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe crude product was purified by flash chromatography (gradient elution 30-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-63909528ddbb494793befa662c8b75eb
Source dataset
uspto-grants-1999_10
Patent number
US05962531

Reaction notes

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