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

HRID 1758443Notes

Reaction equation

HRID 1758443 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 three times 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 benzene-ether to provide 32 g of 3-chlorosulfonyl-4-methoxyphenylacetone.

Workup

  1. extractionextracted three times 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 benzene-ether

Sources & evidence

ORD record
ord-b72f84277f104821a4e62b1425f5e42c
Source dataset
uspto-grants-1983_02
Patent number
US04373106

Reaction notes

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