Hydrogen Peroxide → (-)-cis-Myrtanol

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.

1. customThe reaction mixture was then immersed in a cooling bath
2. customdid not rise over 35° C.
3. temperature(gentle reflux)
4. temperatureThe reaction mixture was then heated
5. temperatureunder reflux for 1 hour
6. extractionThe mixture was extracted with ether (70 ml)
7. washThe ether layer was washed thoroughly with water (3×200 ml)
8. dry with materialThe organic layer was dried over anhydrous potassium carbonate
9. filtrationfiltered
10. concentrationconcentrated
11. distillationDistillation under vacuum

ORD record

ord-8ec558f4c3a24c79a1e71ff38fddd851

Source dataset

uspto-grants-1981_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04298750