Water → HCID 13276514, compound

HRID 2418165Notes

Reaction equation

HRID 2418165 reaction equation
C([S:4][CH:5]([CH2:11][C:12](=[O:26])[C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=O)C.O.S(=O)(=O)(O)O>C(O)C>[SH:4][CH:5]([CH2:11][C:12](=[O:26])[C:13]1[CH:14]=[CH:15][C:16]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:17][CH:18]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 13276506HCID 13276506, compound

Product 1

HCID 13276514HCID 13276514, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.72 g of ethyl 2-acetylthio-3-(4-phenoxybenzoyl)propionate were dissolved in 30 ml of ethanol, then 3 ml of distilled water and 1.2 ml of concentrated sulfuric acid were added, and the mixture was refluxed for 4 hours. The ethanol was removed by evaporation under reduced pressure. Diethyl ether was added to the residue, which was washed with water and dried over magnesium sulfate. The diethyl ether was distilled off and the residue was purified first by silica gel column chromatography, eluted with a mixture of hexane and diethyl ether, then by recrystallization from a mixture of hexane and diethyl ether to give 2.71 g of ethyl 2-mercapto-3-(4-phenoxybenzoyl)propionate.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customThe ethanol was removed by evaporation under reduced pressure
  3. additionDiethyl ether was added to the residue, which
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationThe diethyl ether was distilled off
  7. customthe residue was purified first by silica gel column chromatography
  8. washeluted with a mixture of hexane and diethyl ether
  9. customby recrystallization
  10. additionfrom a mixture of hexane and diethyl ether

Sources & evidence

ORD record
ord-10c36148a580499a92359eac07bc6133
Source dataset
uspto-grants-1984_09
Patent number
US04472316

Reaction notes

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