Water → HCID 13276513, compound

HRID 2418164Notes

Reaction equation

HRID 2418164 reaction equation
C([S:4][CH:5]([CH2:9][C:10](=[O:24])[C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)[C:6]([OH:8])=[O:7])(=O)C.O.S(=O)(=O)(O)O>O1CCOCC1>[SH:4][CH:5]([CH2:9][C:10](=[O:24])[C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:13][CH:12]=1)[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 13276500HCID 13276500, compound

Product 1

HCID 13276513HCID 13276513, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3.44 g of 2-acetylthio-3-(4-phenoxybenzoyl)propionic acid were dissolved in 50 ml of dioxane, then 5 ml of distilled water and 2 ml of concentrated sulfuric acid were added, and the mixture was refluxed for 3 hours. The dioxane was removed by evaporation under reduced pressure. Diethyl ether was added to the residue, which was extracted with a saturated aqueous solution of sodium hydrogencarbonate. The extract was washed with diethyl ether, made slightly acidic by addition of dilute hydrochloric acid, and extracted with diethyl ether. The diethyl ether layer was washed with water and dried over magnesium sulfate. The diethyl ether was distilled off and the residue was purified by first by silica gel column chromatography, eluted with a mixture of hexane and dichloromethane, and then by recrystallization from a mixture of hexane and acetone to give 1.16 g of 2-mercapto-3-(4-phenoxybenzoyl)propionic acid.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. customThe dioxane was removed by evaporation under reduced pressure
  3. additionDiethyl ether was added to the residue, which
  4. extractionwas extracted with a saturated aqueous solution of sodium hydrogencarbonate
  5. washThe extract was washed with diethyl ether
  6. additionmade slightly acidic by addition of dilute hydrochloric acid
  7. extractionextracted with diethyl ether
  8. washThe diethyl ether layer was washed with water
  9. dry with materialdried over magnesium sulfate
  10. distillationThe diethyl ether was distilled off
  11. customthe residue was purified by first by silica gel column chromatography
  12. washeluted with a mixture of hexane and dichloromethane
  13. customby recrystallization
  14. additionfrom a mixture of hexane and acetone

Sources & evidence

ORD record
ord-39b696d1594547ecbd0012a5c3002e19
Source dataset
uspto-grants-1984_09
Patent number
US04472316

Reaction notes

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