Sulfuric Acid → HCID 13647270, compound

HRID 1981873Notes

Reaction equation

HRID 1981873 reaction equation
C([S:4][CH:5]([CH2:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([OH:8])=[O:7])(=O)C.S(=O)(=O)(O)O>C(O)(=O)C>[C:10]([CH2:9][CH:5]([SH:4])[C:6]([OH:8])=[O:7])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 13476426HCID 13476426, compound

Product 1

HCID 13647270HCID 13647270, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2.52 g of 2-acetylthio-3-benzoylpropionic acid in 20 ml of glacial acetic acid was added 4 ml of 10N sulfuric acid, and the mixture was refluxed at heating with stirring for 2 hours. The acetic acid was removed from the mixture by evaporation under reduced pressure, and ethyl acetate was added to the residue. The mixture was washed with water and dried over magnesium sulfate, and the ethyl acetate was removed from the mixture by evaporation. The residue was purified by silica gel column chromatograpy using a mixture of hexane and chloroform as an eluent, and then recrystallized from a mixture of hexane and diethyl ether to give 1.76 g of 3-benzoyl-2-mercaptopropionic acid.

Workup

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

Sources & evidence

ORD record
ord-b7fd6382f802487ca28aad76d7882d3d
Source dataset
uspto-grants-1986_06
Patent number
US04594197

Reaction notes

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