Water → 5-Phenylsulfinylpentyl chloride

HRID 344268Notes

Reaction equation

HRID 344268 reaction equation
[C:1]1([S:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Cl:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:22])C=1.O>ClCCl>[C:1]1([S:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Cl:13])=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 13427894[(5-Chloropentyl)sulfanyl]benzene

Product 1

HCID 541211625-Phenylsulfinylpentyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Phenylthiopentyl chloride (1.84 g) was dissolved in dichloromethane (50 ml), and one equivalent of m-chloroperbenzoic acid was added thereto, which was followed by stirring at room temperature for 6 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 1.20 g of 5-phenylsulfinylpentyl chloride.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cf60e9c9de5d4ddbb2347277e919ddc5
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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