Ethanol → 4-Mercapto-phenyl-acetic acid ethyl ester

HRID 1466927Notes

Reaction equation

HRID 1466927 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:17][CH2:18]O>>[CH2:17]([O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([SH:1])=[CH:7][CH:6]=1)[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 33905114-Mercaptophenylacetic acid

Product 1

HCID 123300434-Mercapto-phenyl-acetic acid ethyl ester

Procedure

To a stirred solution of (4-mercapto-phenyl)-acetic acid (5.0 g, 29.8 mmol) in absolute EtOH (100 mL) at room temperature was added concentrated H2SO4 (10 mL) and the mixture was warmed to reflux. After 4 hrs, the reaction was cooled to room temperature, evaporated under reduced pressure, diluted with DCM (500 mL) and stirred over solid K2CO3. After 1 hr, the resulting mixture was filtered and concentrated to dryness to afford the title compound.

Workup

  1. temperaturethe mixture was warmed to reflux
  2. customevaporated under reduced pressure
  3. additiondiluted with DCM (500 mL)
  4. waitAfter 1 hr
  5. filtrationthe resulting mixture was filtered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9d20ca84f435475c812b0e1b08662f72
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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