Water → (4 t-Butylphenylsulphonyl)nitromethane

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

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%.