Reacción #2025284

Ecuación de reacción

m-chloroperbenzoic acid

sodium hydrogen sulfite

(-)-4-acetyl-4'-(2-acetoxypropyl)biphenyl

CHCl3

m-chloroperbenzoic acid

→

(-)-4-acetoxy-4'-(2-acetoxypropyl)biphenyl

Rendimiento 97.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroprovided with a thermometer
2. 2
   workup.DISSOLUTIONan agitator, and dissolved
3. 3
   Temperaturaat reflux for 8 hours
4. 4
   Lavadothe organic layer was washed with 10% aqueous solution of sodium bicarbonate
5. 5
   Secadowith water, and dried an anhydrous magnesium sulfate
6. 6
   ConcentraciónThe resulting dichloromethane solution was concentrated under the reduced pressure

Procedimiento

29.6 g (0.1 mol) of (-)-4-acetyl-4'-(2-acetoxypropyl)biphenyl (XIX-13) ([α]D20 =-9.9° (C=1, CHCl3)} was charged into a four necked-flask provided with a thermometer and an agitator, and dissolved by adding 200 ml of dichloromethane. 20.7 g (0.12 mol) of m-chloroperbenzoic acid was added in this solution and agitated at reflux for 8 hours. After excess of m-chloroperbenzoic acid was decomposed by adding 10% aqueous solution of sodium hydrogen sulfite to the reaction mixture, the organic layer was washed with 10% aqueous solution of sodium bicarbonate and then with water, and dried an anhydrous magnesium sulfate. The resulting dichloromethane solution was concentrated under the reduced pressure to provide 30.2 g (yield: 97%) of (-)-4-acetoxy-4'-(2-acetoxypropyl)biphenyl (XVIII-13).

Fuente