m-Chloroperbenzoic acid → 2-Oxepanone, 5-(acetyloxy)-
Reaction equation
[C:1]([O:4][CH:5]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]1)(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:20])C=1>C(Cl)(Cl)Cl>[C:1]([O:4][CH:5]1[CH2:6][CH2:7][O:11][C:8](=[O:20])[CH2:9][CH2:10]1)(=[O:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
50 g of 4-acetoxycyclohexanone, dissolved in 150 ml of chloroform, were treated at 40° C. in the course of 40 minutes, with stirring, with 136 g of m-chloroperbenzoic acid (55% strength), dissolved in 500 ml of chloroform. The reaction mixture was stirred at 40° C. for 2 hours. After cooling to room temperature, the precipitated solid (m-chlorobenzoic acid), was filtered off with suction. The chloroform phase was extracted twice by shaking with 20% strength aqueous sodium carbonate solution, dried over sodium sulfate and concentrated on a rotary evaporator. 46.4 g of 4-acetoxycaprolactone (84%, based on the 4-acetoxycyclohexanone employed) were recovered from the residue obtained in this way by bulb tube distillation.