Methanol → alpha-Phenylthio-2-thiopheneacetic acid

HRID 27593Notes

Reaction equation

HRID 27593 reaction equation
[OH-:1].[K+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:11](Cl)(Cl)[CH:12]([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)O.C[OH:22]>>[C:3]1([S:9][CH:12]([C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)[C:11]([OH:22])=[O:1])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 887Methanol2×HCID 7969ThiophenolHCID 14797Potassium HydroxideHCID 12566320alpha-Trichloromethyl-2-thiophenemethanol

Product 1

HCID 23460397alpha-Phenylthio-2-thiopheneacetic acidYield 76%

Procedure

Under an argon atmosphere, potassium hydroxide (1.12 g, 20 mmol) was dissolved in methanol (10 ml). Thiophenol (0.6 g, 5.45 mmol) was added to this solution with stirring and under water cooling. After 10 min., a solution of α-trichloromethyl-2-thiophenemethanol (1.16 g, 5 mmol) in methanol (3 ml) was added. After 10 min., the mixture was gradually heated up and was heated under reflux for 2 hr. with vigorous stirring. After cooling to room temperature and after removal of most of the solvent by distillation under a reduced pressure, diethylether was added and the mixture was decomposed with dilute hydrochloric acid. The ether layer was separated, washed with water, and dried with anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under a reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate: n-hexane=1:4) to give 940 mg of α-phenylthio-2-thiopheneacetic acid as a viscous oil.

Workup

  1. waitAfter 10 min.
  2. temperaturethe mixture was gradually heated up
  3. temperaturewas heated
  4. temperatureunder reflux for 2 hr
  5. customafter removal of most of the solvent
  6. distillationby distillation under a reduced pressure, diethylether
  7. additionwas added
  8. customThe ether layer was separated
  9. washwashed with water
  10. dry with materialdried with anhydrous magnesium sulfate
  11. filtrationAfter filtration
  12. concentrationthe filtrate was concentrated under a reduced pressure
  13. customthe residue was purified by silica gel column chromatography (ethyl acetate: n-hexane=1:4)

Sources & evidence

ORD record
ord-c49a5a66e8e9498c8e752722cf12a997
Source dataset
uspto-grants-1980_09
Patent number
US04221915

Reaction notes

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