Reaction #1909799

ord-bf0ea37fc3f84725a4d5ad4ed5578627

Reaction equation

O=C1OCC(Sc2ccccc2)O1
4-Phenylsulfanyl-[1,3]dioxolan-2-one
O=S([O-])OO.[K+]
OXONE
O
water
O=C1OCC(S(=O)(=O)c2ccccc2)O1
4-benzenesulfonyl-[1,3]dioxolan-2-one

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe obtained reaction mixture
  2. 2
    workup.STIRRINGwas agitated at room temperature for 12 hours
  3. 3
    Otherwas removed
  4. 4
    workup.DISTILLATIONdecompression distillation
  5. 5
    Extractionthe resulting product was extracted
  6. 6
    ExtractionThe extracted organic solvent layer was again extracted
  7. 7
    Otherwas removed
  8. 8
    Otherorganic solvent was removed
  9. 9
    workup.DISTILLATIONdecompression distillation
  10. 10
    OtherUsing silica gel chromatography, separation and purification

Procedure

4-Phenylsulfanyl-[1,3]dioxolan-2-one) was dissolved in methanol, and OXONE® was added. The resulting mixture was agitated at room temperature for 5 minutes and water was added. The obtained reaction mixture was agitated at room temperature for 12 hours. From the agitated reaction mixture, methanol was removed using decompression distillation and the resulting product was extracted using methylene chloride. The extracted organic solvent layer was again extracted using water, moisture was removed using magnesium sulfate, and then organic solvent was removed using decompression distillation. Using silica gel chromatography, separation and purification were performed to obtain a pure target product, 4-benzenesulfonyl-[1,3]dioxolan-2-one.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07037624B2uspto-grants-2006_05