Pyridine → HCID 68296686, compound

Participants

Reaction Conditions

Reaction Steps

100 mg methyl trioxorhenium was dissolved in 30% aqueous hydrogen peroxide (19 ml) and cooled to 0° C. internal in a 250 ml, 3-necked flask. A solution was separately prepared from 1,3-dioxolane (89 ml), the carene mixture (11 g), and pyridine (9 ml). This was also cooled to 0° C. internal. While stirring the cold aqueous solution vigorously, the cold dioxolane solution was added over 70 minutes, keeping the exothermic reaction at 0-5° C. After three hours, NaCl solution (20 ml) was added and the layers were separated. The aqueous layer was extracted once with dioxolane (25 ml). The organics were combined. Aqueous pH 5.8 buffer solution (275 ml) was added and stirred vigorously at room temperature for 1 hour, then 30° C. for 2.5 hours. The reaction was transferred to a separating funnel and washed once with heptane (100 ml). NaCl (43 g) was added to the aqueous layer and stirred for 30 min. The aqueous layer was extracted with ethyl acetate (1×100 ml, 2×250 ml). The ethyl acetate extracts were combined, dried over Na2SO4, and concentrated in vacuo to solid (2 g). The solid was dissolved in hot ethyl acetate. Heptane was added and the solution was allowed to cool with stirring and then cooled to 0° C. The solid was collected by vacuum filtration and washed with hexane. After drying under vacuum, 1.1 g (+)-p-menth-2-ene-diol (6.5% yield from (+)-3-carene) was obtained.

Provenance & Evidence