Water → 4-(Methylsulfonyl)phenol

HRID 1081254Notes

Reaction equation

HRID 1081254 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.I([O-])(=O)(=O)=[O:11].[Na+].[OH2:16]>CO>[CH3:1][S:2]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)(=[O:11])=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 140864-(Methylthio)phenolHCID 23667635Sodium periodate3×

Product 1

HCID 1233504-(Methylsulfonyl)phenolYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
4 °C

Procedure

To a solution of 4-(methylthio)phenol (7.0 g. 0.05 mol) in 30% aqueous methanol (100 ml) at 0° C. is added a solution of sodium periodate (10.7 g, 0.05 mmol) and the resulting suspension is stirred for 30 min. Water (500 ml) is then added and the precipitate removed by filtration. The filtrate is cooled to 4° C. and a further portion of sodium periodate (10.7 g, 0.05 mmol) added and the resulting suspension stirred for 48 h when a further portion of sodium periodate (5.35 g, 0.025 mmol) is added. After stirring for a further 18 h, the precipitate is removed by filtration, the filtrate extracted with ether which is evaporated to dryness and the residue is purified on a silica column using chloroform methanol, 9:1, as eluent to give the title compound (2.75 g, 32% yield).

Workup

  1. customthe precipitate removed by filtration
  2. additionis added
  3. stirringAfter stirring for a further 18 h
  4. customthe precipitate is removed by filtration
  5. extractionthe filtrate extracted with ether which
  6. customis evaporated to dryness
  7. customthe residue is purified on a silica column

Sources & evidence

ORD record
ord-f1ac90a460fe4c2ea4c3c9e74f0e2d2d
Source dataset
uspto-grants-1996_12
Patent number
US05585364

Reaction notes

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