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

HRID 2399249Notes

Reaction equation

HRID 2399249 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 benzene-ether 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 benzene-ether

Sources & evidence

ORD record
ord-fb93a23091c3446694358d8d8e102e6d
Source dataset
uspto-grants-1995_09
Patent number
US05447958

Reaction notes

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