Potassium Hydroxide → 4-Mercaptophenylacetic acid

HRID 1777818Notes

Reaction equation

HRID 1777818 reaction equation
C(OC([S:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)=S)C.[OH-].[K+]>CCO.O>[SH:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 87073696HCID 87073696, compound

Product 1

HCID 33905114-Mercaptophenylacetic acidYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(4-((ethoxycarbonothioyl)thio)phenyl)acetic acid (50.0 g, crude, 0.195 mol) in EtOH (180 mL) was added a solution of KOH (40.5 g, 0.724 mol) in water (180 mL). The mixture was stirred at reflux overnight. The mixture was concentrated under reduced pressure to remove EtOH. The aqueous phase was adjusted to pH=1˜2 with conc. HCl. The aqueous phase was then extracted with ethyl acetate (3×200 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude 2-(4-mercaptophenyl)acetic acid (32.0 g, 98%) as a gray solid, which was used for next step directly without further purification. 1H NMR (purified by pre-TLC, CD3OD, 400 MHz): δ 7.23 (d, J=8.4 Hz, 2H), 7.15 (d, J=8.0 Hz, 2H), 3.54 (s, 2H).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto remove EtOH
  4. extractionThe aqueous phase was then extracted with ethyl acetate (3×200 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ecbe0ee865504bf38e42d7f8b9e1357a
Source dataset
uspto-grants-2016_02
Patent number
US09266886B2

Reaction notes

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