Chlorosulfonic acid → 2-Methoxy-5-(2-oxopropyl)benzenesulfonyl chloride

HRID 569287Notes

Reaction equation

HRID 569287 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15](=[O:17])[CH3:16])=[CH:10][CH:9]=1>>[Cl:1][S:2]([C:13]1[CH:12]=[C:11]([CH2:14][C:15](=[O:17])[CH3:16])[CH:10]=[CH:9][C:8]=1[O:7][CH3:6])(=[O:5])=[O:3]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 312311-(p-Methoxyphenyl)-2-propanone

Product 1

HCID 131062582-Methoxy-5-(2-oxopropyl)benzenesulfonyl chlorideYield 40%

Procedure

To 250 g of chlorosulfonic acid was added dropwise 50 g of 4-methoxyphenylacetone at 0°-5° C. After stirring the mixture for 4 hours at room temperature, the reaction mixture was poured into 2,500 ml of ice water and extracted thrice with 500 ml of ethyl acetate. The extract was washed with water and after drying the extract with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The crude crystals obtained were recrystallized from benzeneether to provide 32 g of 3-chlorosulfonyl-4-methoxyphenylacetone.

Workup

  1. extractionextracted thrice with 500 ml of ethyl acetate
  2. washThe extract was washed with water
  3. customafter drying the
  4. extractionextract with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe crude crystals obtained
  7. customwere recrystallized from benzeneether

Sources & evidence

ORD record
ord-3d779e9c0ffc4dd483ac84d50ee08781
Source dataset
uspto-grants-1988_03
Patent number
US04731478

Reaction notes

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