Water → 4-(Methylsulfonyl)phenol

HRID 361699Notes

Reaction equation

HRID 361699 reaction equation
S([O-])(O[O-])(=O)=[O:2].[K+].[K+].OOS([O-])=O.[K+].[CH3:15][S:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.[OH2:24]>CO>[CH3:15][S:16]([C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)(=[O:2])=[O:24]

Participants

6

Reactant 4

HCID 962Water2×HCID 140864-(Methylthio)phenolHCID 10313463Potassium peroxymonosulphateHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 1233504-(Methylsulfonyl)phenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of potassium peroxymonosulphate (120 g) in the form of OXONE (Trademark) in water (100 ml) was slowly added to a solution of 4-methylmercaptophenol (15 g) in methanol (50 ml). The reaction mixture was stirred for 2 hours. Water (500 ml) was added and the resulting mixture extracted with ethyl acetate (200 ml and 100 ml). The ethyl acetate extracts were combined, washed with water (800 ml), dried (MgSO4) and evaporated to give 4-methylsulphonylphenol (11.54 g) as a colourless oil which slowly crystallised on standing, NMR(CDCl3): 3.06(3H,s), 6.80(1H,s), 6.98(2H,d) and 7.79(2H,d); m/z 190 (M+NH4).

Workup

  1. extractionthe resulting mixture extracted with ethyl acetate (200 ml and 100 ml)
  2. washwashed with water (800 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-a30d9772558d4562b77889ffa8f41e83
Source dataset
uspto-grants-1999_02
Patent number
US05866611

Reaction notes

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