Hydrogen Peroxide → Gamma-Decalactone

HRID 1105509Notes

Reaction equation

HRID 1105509 reaction equation
C=[CH:2][CH2:3][CH2:4][CH:5]([OH:12])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[O:13]=[O+][O-].O=O.OO.[OH-].[Na+]>CO>[C:2]1(=[O:13])[O:12][CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:4][CH2:3]1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 977OxygenHCID 14798Sodium HydroxideHCID 24823OzoneHCID 104422311-Undecen-5-ol

Product 1

HCID 12813Gamma-DecalactoneYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-undecen-5-ol (8.5 g., 0.005 mol) dissolved in methanol (100 mL) was ozonized while being cooled in a dry ice-isopropanol bath. Upon completion of ozonolysis, excess ozone was expelled with a stream of oxygen, the ozonide was then treated with 50% H2O2 (10 ml) and 10% sodium hydroxide (40 ml) at room temperature for 20 hour. Acidification and extraction with methylene chloride yielded a product which was distilled to give 4-decanolide (5.5 g., 65% yield; b.p. 140°-145°/10 torr).

Workup

  1. temperaturewhile being cooled in a dry ice-isopropanol bath
  2. extractionAcidification and extraction with methylene chloride
  3. customyielded a product which
  4. distillationwas distilled

Sources & evidence

ORD record
ord-7ec6a4da06a74fb6a880b6c4155976fa
Source dataset
uspto-grants-1982_01
Patent number
US04309352

Reaction notes

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