Sulfuric Acid → HCID 23317882, compound

HRID 1981875Notes

Reaction equation

HRID 1981875 reaction equation
C([S:4][CH:5]([CH2:11][C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=O)C.S(=O)(=O)(O)O>C(O)C>[C:12]([CH2:11][CH:5]([SH:4])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 23317879HCID 23317879, compound

Product 1

HCID 23317882HCID 23317882, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2.80 g of ethyl 2-acetylthio-3-benzoylpropionate in 30 ml of ethanol was added 4 ml of 10N sulfuric acid, and the mixture was refluxed at heating with stirring for 4 hours. The ethanol was removed from the mixture by evaporation under redused pressure, and diethyl ether was added to the residue. The mixture was washed with water and dried over magnesium sulfate. The diethyl ether was removed from the mixture by evaporation, and the residue was purified by silica gel column chromatography using a mixture of hexane and diethyl ether as an eluent to give 1.62 g of ethyl 3-benzoyl-2-mercaptopropionate as an oil.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureat heating
  3. customThe ethanol was removed from the mixture by evaporation under redused pressure, and diethyl ether
  4. additionwas added to the residue
  5. washThe mixture was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customThe diethyl ether was removed from the mixture by evaporation
  8. customthe residue was purified by silica gel column chromatography
  9. additiona mixture of hexane and diethyl ether as an eluent

Sources & evidence

ORD record
ord-5d52e8d8fa7743b99b8e3f4c298bc44a
Source dataset
uspto-grants-1986_06
Patent number
US04594197

Reaction notes

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