Acetic Acid → {[(Benzenesulfinyl)methyl]sulfanyl}benzene

HRID 437111

Reaction equation

HRID 437111 reaction equation
C(O)(=[O:3])C.[C:5]1([S:11][CH2:12][S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.OO.C(=O)([O-])[O-].[K+].[K+]>O.C(Cl)Cl>[C:14]1([S:13][CH2:12][S:11]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:3])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 770971,1'-(Methylenebis(thio))bis(benzene)

Product 1

HCID 12743411{[(Benzenesulfinyl)methyl]sulfanyl}benzeneYield 96.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5 ml of acetic acid was added to 1.538 g of bis(phenylthio)methane, 0.75 ml of an aqueous solution of hydrogen peroxide (concentration: 30%) was added thereto, and then the mixture was stirred for 1 hour at room temperature. After 100 ml of methylene chloride, 6 g of potassium carbonate and a small amount of water were thereto, the resultant mixture was dried with anhydrous sodium sulfate. The product was concentrated under reduced pressure, and then the leavings were separated by means of column-chromatography (silica gel, methylene chloride). Thus 1.585 g of phenyl phenylthiomethyl sulfoxide was obtained as a colorless liquid. The yield was 96.6%.

Workup

  1. additionwas added
  2. dry with materialthe resultant mixture was dried with anhydrous sodium sulfate
  3. concentrationThe product was concentrated under reduced pressure
  4. customthe leavings were separated by means of column-chromatography (silica gel, methylene chloride)

Sources & evidence

ORD record
ord-5fe393eb309e46adaf0668e4008589b9
Source dataset
uspto-grants-1977_06
Patent number
US04029712

Linked notes

Loading…