Reaction #55871

Reaction equation

α-trichloromethyl-2-thiophenemethanol

methanol

potassium hydroxide

methanol

Thiophenol

→

α-phenylthio-2-thiopheneacetic acid

Yield 76.0%

Conditions

Workup

1. 1
   workup.WAITAfter 10 min.
2. 2
   Temperaturethe mixture was gradually heated up
3. 3
   Temperaturewas heated
4. 4
   Temperatureunder reflux for 2 hr
5. 5
   Otherafter removal of most of the solvent
6. 6
   workup.DISTILLATIONby distillation under a reduced pressure, diethylether
7. 7
   workup.ADDITIONwas added
8. 8
   OtherThe ether layer was separated
9. 9
   Washwashed with water
10. 10
    Dryingdried with anhydrous magnesium sulfate
11. 11
    FiltrationAfter filtration
12. 12
    Concentrationthe filtrate was concentrated under a reduced pressure
13. 13
    Otherthe residue was purified by silica gel column chromatography (ethyl acetate: n-hexane=1:4)

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.

Source