Hydrogen Peroxide → HCID 20354850, compound

HRID 1580780Notes

Reaction equation

HRID 1580780 reaction equation
[C:1]([O:4][CH:5]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:6][CH2:7][C:8]1[C:9](=[O:13])[CH2:10][CH2:11][CH:12]=1)(=[O:3])[CH3:2].[OH:19]O.[OH-].[Na+]>CO>[C:1]([O:4][CH:5]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:6][CH2:7][C:8]12[O:19][CH:12]1[CH2:11][CH2:10][C:9]2=[O:13])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 20354852HCID 20354852, compound

Product 1

HCID 20354850HCID 20354850, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 2-(3-acetoxyoctyl)cyclopent-2-enone (31.8 g.) [prepared as described in (f) above] in methanol (700 ml.) was treated slowly with aqueous hydrogen peroxide solution (45 ml. of "100 vol." solution) and aqueous 4N sodium hydroxide solution (15 ml.) at 5° to 10°C. and allowed to stand at room temperature for 18 hours. The solution was concentrated in vacuo (to about 100 ml. volume), and water (100 ml.) was added to the residue. The mixture was extracted with chloroform and the chloroform extract was washed with water and dried over magnesium sulphate. The solvent was removed in vacuo to give 2-(3-acetoxyoctyl)-2,3-epoxycyclopentanone (26.4 g.) which was used as starting material in the following preparation (h) of 5-acetoxy-2-(3-acetoxyoctyl)-cyclopent-2-enone without further purification.

Workup

  1. concentrationThe solution was concentrated in vacuo (to about 100 ml. volume), and water (100 ml.)
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with chloroform
  4. extractionthe chloroform extract
  5. washwas washed with water
  6. dry with materialdried over magnesium sulphate
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0af2a2bb873b4c3595e7e19181cbcd54
Source dataset
uspto-grants-1976_01
Patent number
US03933890

Reaction notes

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