Formic Acid → ((4-Chlorobutyl)sulfonyl)benzene

HRID 344266Notes

Reaction equation

HRID 344266 reaction equation
OO.[C:3]1([S:9][CH2:10][CH2:11][CH2:12][CH2:13][Cl:14])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-:15].[Na+].C(O)=[O:18]>>[C:3]1([S:9]([CH2:10][CH2:11][CH2:12][CH2:13][Cl:14])(=[O:18])=[O:15])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 284Formic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 13107770[(4-Chlorobutyl)sulfanyl]benzene

Product 1

HCID 12457347((4-Chlorobutyl)sulfonyl)benzene

Procedure

30% Aqueous hydrogen peroxide solution (27.6 ml) was dropwise added under ice-cooling to a solution of 4-phenylthiobutyl chloride (22.2 g) obtained in the same manner as in Preparation Example 99 in formic acid (150 ml), which was followed by stirring at room temperature for 1 hr. The reaction mixture was poured into ice water, neutralized with sodium hydroxide solution and extracted with chloroform. 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 (chloroform) and further recrystallized from hexane to give 21 g of 4-phenylsulfonylbutyl chloride.

Workup

  1. extractionextracted with chloroform
  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 (chloroform)
  6. customfurther recrystallized from hexane

Sources & evidence

ORD record
ord-cf72122fd2ad4bfbb27ac5f29b030c7b
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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