Acetic Acid → HCID 11095779, compound

HRID 1290776Notes

Reaction equation

HRID 1290776 reaction equation
[CH:1]1([S:7][CH2:8][CH2:9][CH2:10][OH:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:12].[Na+].C(O)(=[O:16])C>>[CH:1]1([S:7]([CH2:8][CH2:9][CH2:10][OH:11])(=[O:16])=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 23282670HCID 23282670, compound

Product 1

HCID 11095779HCID 11095779, compound

Procedure

To a solution of 3-cyclohexylthio-1-propanol (60 g) in glacial acetic acid (250 ml) hydrogen peroxide (35% in water, 210 ml) was added at 10° C. followed by reflux for 2 h. After cooling the mixture was poured onto ice followed by extraction with ethyl acetate (1 l). The organic phase was washed several times with 1M sodium hydroxide. Removal of solvent gave an oil which was treated at reflux temperature with 1M sodium hydroxide (600 ml) for 1 h. Extraction with ethyl acetate, drying of the organic phase over magnesium sulfate, and removal of solvent in vacuo gave a colorless oil (37 g) of 3-cyclohexylsulfonyl-1-propanol which was used without further purification in the next step.

Workup

  1. temperatureby reflux for 2 h
  2. temperatureAfter cooling the mixture
  3. additionwas poured onto ice
  4. extractionfollowed by extraction with ethyl acetate (1 l)
  5. washThe organic phase was washed several times with 1M sodium hydroxide
  6. customRemoval of solvent
  7. customgave an oil which
  8. additionwas treated
  9. extractionExtraction with ethyl acetate
  10. dry with materialdrying of the organic phase over magnesium sulfate, and removal of solvent in vacuo

Sources & evidence

ORD record
ord-abd9c8424e104a699fb86fb3c8137770
Source dataset
uspto-grants-1998_05
Patent number
US05753661

Reaction notes

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