m-Chloroperbenzoic acid → 2-Oxepanone, 5-(acetyloxy)-

HRID 1975501Notes

Reaction equation

HRID 1975501 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

HCID 70297m-Chloroperbenzoic acidHCID 5658694-Oxocyclohexyl acetate

Product 1

HCID 117450862-Oxepanone, 5-(acetyloxy)-

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

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.

Workup

  1. additionwere treated at 40° C. in the course of 40 minutes
  2. temperatureAfter cooling to room temperature
  3. filtrationthe precipitated solid (m-chlorobenzoic acid), was filtered off with suction
  4. extractionThe chloroform phase was extracted twice
  5. stirringby shaking with 20% strength aqueous sodium carbonate solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated on a rotary evaporator
  8. customwere recovered from the residue
  9. customobtained in this way by bulb tube
  10. distillationdistillation

Sources & evidence

ORD record
ord-cf1a49212fca42f098797800ba0766fe
Source dataset
uspto-grants-1994_02
Patent number
US05286875

Reaction notes

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