Water → (4 t-Butylphenylsulphonyl)nitromethane

HRID 465493Notes

Reaction equation

HRID 465493 reaction equation
S([O-])(O[O-])(=O)=[O:2].[K+].[K+].[C:9]([C:13]1[CH:18]=[CH:17][C:16]([S:19][CH2:20][N+:21]([O-:23])=[O:22])=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10].[OH2:24]>CO>[C:9]([C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH2:20][N+:21]([O-:23])=[O:22])(=[O:2])=[O:24])=[CH:15][CH:14]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 962Water2×HCID 10313463Potassium peroxymonosulphateHCID 14404080(4-t-Butylphenylthio)nitromethane

Product 1

HCID 14404081(4 t-Butylphenylsulphonyl)nitromethane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of potassium peroxymonosulphate [`Oxone` (trade mark); 38.7 g, 63 mmol]in water (100 ml) was added in one portion to a vigorously stirred solution of (4-t-butylphenylthio)nitromethane (A) (4.76 g, 21.9 mmol) in methanol (90 ml). A cream coloured precipitate was formed. The mixture was stirred overnight. Water (200 ml) was then added and the mixture was extracted with ethyl acetate. The extracts were combined, dried (MgSO4) and the solvent was removed by evaporation. The residual yellow solid was recrystallised from cyclohexane to give (4 t-butylphenylsulphonyl)nitromethane, as a colourless solid (3.34 g), m.p. 90°-91° C., microanalysis found: C, 51.4; H, 5.9; N, 5.4%; C11H15NO4S: requires: C, 51.4; H, 5.9; N, 5.4%.

Workup

  1. customwas formed
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialdried (MgSO4)
  4. customthe solvent was removed by evaporation
  5. customThe residual yellow solid was recrystallised from cyclohexane

Sources & evidence

ORD record
ord-c2ebd40050344b869d0cf8bec5195fba
Source dataset
uspto-grants-1992_10
Patent number
US05153227

Reaction notes

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