Hydrochloric Acid → 5-Benzenesulfonylpentan-2-one

HRID 1984468Notes

Reaction equation

HRID 1984468 reaction equation
Cl.[C:2]1([S:8]([CH2:11][CH2:12][CH:13]([C:19](=[O:21])[CH3:20])C(OCC)=O)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C>[C:2]1([S:8]([CH2:11][CH2:12][CH2:13][C:19](=[O:21])[CH3:20])(=[O:9])=[O:10])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66959018Ethyl 2-(2-benzenesulfonylethyl)-3-oxo-butyrate

Product 1

HCID 3456215-Benzenesulfonylpentan-2-oneYield 97.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrochloric acid was added (150 mL of 3 N) to a solution of ethyl 2-(2-benzenesulfonylethyl)-3-oxo-butyrate (21.7 g, 76.3 mmol) in 100 mL of ethanol and heated to reflux overnight. The reaction was cooled to ambient temperature and the mixture was concentrated under reduced pressure. The residue was extracted with several portions of ethyl acetate, and the combined organic layers were washed with saturated aqueous sodium bicarbonate, washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 16.8 g of 5-benzenesulfonylpentan-2-one as a yellow oil.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. concentrationthe mixture was concentrated under reduced pressure
  4. extractionThe residue was extracted with several portions of ethyl acetate
  5. washthe combined organic layers were washed with saturated aqueous sodium bicarbonate
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b5de26c84bd64574aae98ae760896e65
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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