Water → 4-[(4-Hydroxyphenyl)disulfanyl]phenol

HRID 1028325Notes

Reaction equation

HRID 1028325 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[OH2:9]>CS(C)=O.C(OCC)C>[S:8]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1)[S:8][C:5]1[CH:6]=[CH:7][C:2]([OH:9])=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 962WaterHCID 2401474-Mercaptophenol

Product 1

HCID 2806654-[(4-Hydroxyphenyl)disulfanyl]phenolYield 96%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

25.0 g of para-hydroxy thiophenol (Wako Pure Chemical Industries, Ltd.) was dissolved in 100 ml of dimethyl sulfoxide (Kanto Chemical Co., Ltd.) at 0 degree C. The reaction solution was stirred for 24 hours at 65 degree C. and cooled to 0 degree C. after the completion of the reaction. Then the mixture was diluted with 100 ml of diethyl ether (Wako Pure Chemical Industries, Ltd.). Water was added to this solution and the aqueous phase was extracted with 50 ml of diethyl ether three times. Then the organic phase was dried by using sodium sulfate (Wako Pure Chemical Industries, Ltd.) and recrystallized in chloroform (Wako Pure Chemical Industries, Ltd.). 4,4′-disulfanediyldiphenol was obtained (23.8 g, yield 96%).

Workup

  1. temperatureand cooled to 0 degree C
  2. customafter the completion of the reaction
  3. extractionthe aqueous phase was extracted with 50 ml of diethyl ether three times
  4. customThen the organic phase was dried
  5. customrecrystallized in chloroform (Wako Pure Chemical Industries, Ltd.)

Sources & evidence

ORD record
ord-7f77600ac09d4df79a3beb366ca3c272
Source dataset
uspto-grants-2014_05
Patent number
US08735522B2

Reaction notes

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