Acetone → 2-Methanesulfonylphenol

HRID 724610Notes

Reaction equation

HRID 724610 reaction equation
CS[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].O[O:11][S:12]([O-:14])=O.[K+].[CH3:16]C(C)=O>O>[CH3:16][S:12]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])(=[O:14])=[O:11]

Participants

5

Reactant 3

HCID 180AcetoneHCID 61261o-(Methylthio)phenolHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 5989982-MethanesulfonylphenolYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(Methylthio)phenol (1.08 g, 7.32 mmol) was dissolved in acetone (20 mL). Oxone® (9.4 g, 15 mmol) was separately dissolved in water (100 mL) and stirred at ambient temperature for 24 h. The acetone was concentrated, extracted with ether, dried over sodium sulfate, filtered, and concentrated to yield a waxy solid (1.2 g, 95%). 1H NMR (400 MHz, CDCl3): δ 8.85 (s, 1H), 7.69 (dd, J=8.4 Hz, J′=1.7 Hz, 1H), 7.54 (m, 1H), 7.05 (m, 2H), 3.12 (s, 3H); LCMS found for C7H9O3S (M+H)+: m/z=173.0.

Workup

  1. concentrationThe acetone was concentrated
  2. extractionextracted with ether
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-77679204bffc4960a8b7a0b6dd22dae1
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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