Hydrogen Peroxide → Cyclopentane, 1-acetyl-1,2-epoxy-

HRID 1578807Notes

Reaction equation

HRID 1578807 reaction equation
[C:1]([C:4]1[CH2:8][CH2:7][CH2:6][CH:5]=1)(=[O:3])[CH3:2].[OH:9]O.[OH-].[Na+]>CO.O>[C:1]([C:4]12[O:9][CH:5]1[CH2:6][CH2:7][CH2:8]2)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 1929251-Acetylcyclopentene

Product 1

HCID 537123Cyclopentane, 1-acetyl-1,2-epoxy-

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 11.02 g of 1-acetyl-cyclopent-1-ene in 50 ml of methanol is cooled to -10°C and mixed with 28.8 ml of perhydrol within 5 minutes. In the course of 1 hour, while stirring and cooling, 8.25 ml of 6N-sodium hydroxide solution are added, the whole is stirred for 1/2 hour at room temperature, diluted with 125 ml of water and extracted with pentane. The pentane solution is washed neutral with sodium chloride solution and the pentane is distilled off through a Vigreux column. The residue is distilled under 10 mm Hg pressure, to yield 1-acetyl-1,2-epoxy-cyclopentane passing over at 62° - 63°C.

Workup

  1. temperaturecooling
  2. stirringthe whole is stirred for 1/2 hour at room temperature
  3. extractionextracted with pentane
  4. washThe pentane solution is washed neutral with sodium chloride solution
  5. distillationthe pentane is distilled off through a Vigreux column
  6. distillationThe residue is distilled under 10 mm Hg pressure

Sources & evidence

ORD record
ord-c72dce79878e4d71943d180cc5d16560
Source dataset
uspto-grants-1976_02
Patent number
US03939207

Reaction notes

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