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

HRID 1863294Notes

Reaction equation

HRID 1863294 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

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 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.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with three 100 ml portions of chloroform
  3. washThe combined extracts are washed with three 100 ml portions of water, 100 ml of saturated NaHCO3, saturated brine
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvent
  6. customaffords an oil which
  7. customcrystallizes

Sources & evidence

ORD record
ord-c502d7deaf7f40459af74660b41e5659
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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