Acetic Acid → Methyl [p-(p-chlorophenylsulfonyl)phenyl]acetate

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C(O)(=[O:22])C.OO.[OH2:26]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=2)(=[O:22])=[O:26])=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 176Acetic Acid

HCID 784Hydrogen Peroxide

HCID 962Water

HCID 12531842Methyl [p-(p-chlorophenylthio)phenyl]acetate

Product 1

HCID 53805964Methyl [p-(p-chlorophenylsulfonyl)phenyl]acetate

Conditions

Temperature: 70 °C

Procedure

A mixture of 14.62 g of methyl [p-(p-chlorophenylthio)phenyl]acetate, 100 ml of glacial acetic acid and 62.5 ml of 30% hydrogen peroxide is heated to 70° C. and kept at 70° C. for 3 hours. After cooling, the mixture is poured into 500 ml of water and extracted with three 100 ml portions of chloroform. The combined extracts are washed with three 100 ml portions of water, 100 ml of saturated NaHCO3, saturated brine and dried over MgSO4. Evaporation of the solvent affords an oil which crystallizes on standing to give 14.9 g of product as white crystals (from petroleum ether) mp 78°-80° C.