Hydrogen Peroxide → Gamma-Decalactone

Participants

Reaction Steps

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).

Provenance & Evidence