Hydrogen Peroxide → Bis(p-chlorophenyl)disulfide

HRID 1584547Notes

Reaction equation

HRID 1584547 reaction equation
ClC([S:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)Cl.O.OO>CO>[CH:10]1[C:5]([S:4][S:4][C:5]2[CH:6]=[CH:7][C:8]([Cl:11])=[CH:9][CH:10]=2)=[CH:6][CH:7]=[C:8]([Cl:11])[CH:9]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 158696321-Chloro-4-[(dichloromethyl)sulfanyl]benzene

Product 1

HCID 14360Bis(p-chlorophenyl)disulfideYield 93.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A 1-liter, 4-necked flask equipped with a stirrer, thermometer, condenser and gas inlet tube was charged with 227.5 g (1.00 mole) of 4-chlorophenyl dichloromethyl sulfide, 50 g of water and 500 g of methanol. The mixture was heated to 70° C. for 5 hours to complete hydrolysis. After completion of the reaction, 357 g (1.05 moles) of 10% aqueous solution of hydrogen peroxide was added dropwise at 40° C. over a period of 1 hour. The mixture was stirred for 1 hour at the same temperature. The precipitated crystals were filtered, giving 134.7 g of 4,4'-dichlorodiphenyl disulfide in a yield of 93.9% based on 4-chlorophenyl dichloromethyl sulfide.

Workup

  1. customA 1-liter, 4-necked flask equipped with a stirrer
  2. customhydrolysis
  3. additionwas added dropwise at 40° C. over a period of 1 hour
  4. filtrationThe precipitated crystals were filtered

Sources & evidence

ORD record
ord-53d2002fdd744763bcf85e47a4877a32
Source dataset
uspto-grants-1999_08
Patent number
US05932731

Reaction notes

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