Reaction #2006423

Reaction equation

4-vinyl-benzoic acid

benzenethiol

VAZO

→

white solid

Yield 85.0%

4-(2-Thiophenyl)-ethyl Benzoic Acid

Yield 85.0%

Solvents

benzene

Conditions

Workup

1. 1
   OtherAccording to the published procedure (Gareau et al., Tet. Lett., 1994, 1837), under nitrogen atmosphere in a 50 mL round bottomed flask
2. 2
   Temperatureat reflux
3. 3
   Otherthe solvent was evaporated under vacuo
4. 4
   OtherThe solid was purified by trituration

Procedure

According to the published procedure (Gareau et al., Tet. Lett., 1994, 1837), under nitrogen atmosphere in a 50 mL round bottomed flask containing 4-vinyl-benzoic acid (1.0 g, 6.75 mmoles) in 10 mL of benzene (0.7 M) was added benzenethiol (797 μL, 7.76 mmoles) followed by VAZO™ (Aldrich Chemical Company, 495 mg, 2.02 mmoles). The mixture was stirred for 12 hours at reflux. The resulting solution was cooled at room temperature and the solvent was evaporated under vacuo. The solid was purified by trituration using hexane and dichloromethane to afford 1.94 g (85%) of white solid.

Source