Water → 4-(Methylsulfonyl)phenol

HRID 1420816Notes

Reaction equation

HRID 1420816 reaction equation
[OH:1]OS([O-])=O.[K+].[CH3:7][S:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.[OH2:16]>CO>[CH3:7][S:8]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)(=[O:1])=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 140864-(Methylthio)phenolHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 1233504-(Methylsulfonyl)phenolYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Oxone (65.8 g, 0.108 mol) in water (290 ml) was added to a cooled (ice-bath) solution of 4-(methylmercapto)phenol (5 g, 36 mmol) in methanol (290 ml). The resulting solution was stirred at ambient temperature for 48 h. and then concentrated in vacuo. The residue was diluted with water (100 ml) and extracted with dichloromethane (10×100 ml). The combined organic layers were dried over sodium sulphate and removal of the solvent in vacuo gave the title compound as a clear oil (5.66 g, 92%). 1H NMR (250 MHz, CDCl3) δ7.80-7.75 (2H, d, J 11.7 Hz), 7.28 (1H, br s), 7.01-6.96 (2H, d, J 11.7 Hz), and 3.08 (3H, s).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with water (100 ml)
  3. extractionextracted with dichloromethane (10×100 ml)
  4. dry with materialThe combined organic layers were dried over sodium sulphate and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-1cae6726abc242b08de2338a23245fad
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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