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

HRID 1889168Notes

Reaction equation

HRID 1889168 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.S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[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

Conditions

Temperature
60 °C

Procedure

To a solution of 4-mercapto-phenyl acetic acid (5 gm, 29.72 mmol) in ethanol (60 ml) was added sulfuric acid (1.58 ml, 29.72 mmol) dropwise. Reaction mixture was then heated at 60° C. for 3 hr, concentrated to remove ethanol. The residue was neutralized with satd. aq. NaHCO3 solution and extracted with ethyl acetate (3×30 ml) washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to provide (4-mercapto-phenyl)-acetic acid ethyl ester (5.5 gm).

Workup

  1. customReaction mixture
  2. concentrationconcentrated
  3. customto remove ethanol
  4. extractionaq. NaHCO3 solution and extracted with ethyl acetate (3×30 ml)
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-68e751bebf1b4033b71c91efbd62eed4
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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