Hydrogen Peroxide → 1-(p-Chlorophenylsulfinyl)-3-chloropropane

HRID 1614615Notes

Reaction equation

HRID 1614615 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][CH2:11][Cl:12])=[CH:4][CH:3]=1.OO.S(=O)(=O)(O)[OH:16]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH2:9][CH2:10][CH2:11][Cl:12])=[O:16])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 2235371-Chloro-4-[(3-chloropropyl)sulfanyl]benzene

Product 1

HCID 197720711-(p-Chlorophenylsulfinyl)-3-chloropropane

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 206.76 g (0.44 mol) of 1-chloro-4-[(3-chloropropyl)thio]benzene (J.A.C.S. 82, 2505, 1960) and 111.50 g of 30% H2O2 (0.98 mol) in 1 L of acetone chilled in a dry ice acetone bath was added 90 mL of concentrated sulfuric acid. The ice bath was removed and the mixture stirred at ambient temperature for 16 hr. The mixture was diluted with 1 L of water and extracted with two 500 mL portions of CH2Cl2. The extracts were dried (MgSO4) and concentrated separately and the residual material from both extractions shown to be a mixture of product and starting material. The impure product was chromatographed on Florisil (4×75 cm) using petroleum ether-chloroform for elution. The yield was 50.36 g.

Workup

  1. customThe ice bath was removed
  2. additionThe mixture was diluted with 1 L of water
  3. extractionextracted with two 500 mL portions of CH2Cl2
  4. dry with materialThe extracts were dried (MgSO4)
  5. concentrationconcentrated separately
  6. extractionthe residual material from both extractions
  7. additiona mixture of product
  8. customThe impure product was chromatographed on Florisil (4×75 cm)
  9. washfor elution

Sources & evidence

ORD record
ord-df6d1b4553ce4dfea6350db640d831a8
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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