Hydrogen Peroxide → (-)-cis-Myrtanol

Participants

Reaction Steps

Hydroboration was carried out by adding (-)-B-pinene (11.9 ml, 75 mmol, 95.5% optical purity) dropwise to a well-stirred mixture of borane-1,4-thioxane (3.13 ml, 25 mmol) and pentane (18.3 ml) at room temperature (under nitrogen). The solution was allowed to stand for 15 min. to complete the hydroboration. Then ethanol (15 ml) was added, followed by 3 M sodium hydroxide (25.0 ml, 75 mmol). The reaction mixture was then immersed in a cooling bath and 30% aqueous hydrogen peroxide (9.4 ml, 75 mmol) was added dropwise over 15 min. at such a rate that the temperature did not rise over 35° C. (gentle reflux). The reaction mixture was then heated under reflux for 1 hour and then poured into ice-water (300 ml). The mixture was extracted with ether (70 ml). The ether layer was washed thoroughly with water (3×200 ml), followed by saturated brine solution (50 ml). The organic layer was dried over anhydrous potassium carbonate, filtered, and concentrated. Distillation under vacuum provided pure (-)-cis-myrtanol: 9.0 g, a yield of 79%; b.p. 68°-69° C.

Provenance & Evidence