Hydrogen Peroxide → 2,2-Dicyclopropylethan-1-ol

Participants

Reaction Steps

Dicyclopropyl ethylene (19 g, 0.176 mole) was dissolved in dry tetrahydrofuran (100 ml) in a three-neck flask under nitrogen and treated with borane-tetrahydrofuran in tetrahydrofuran (1M, 210 ml). The mixture was stirred at room temperature for 4 hours before adding cautiously (foaming occurs) 3N sodium hydroxide (60 ml). After addition was complete, aqueous hydrogen peroxide (30%, 60 ml) was added dropwise at a rate sufficient to maintain reflux. When addition was complete, the mixture was refluxed for a further 30 minutes, cooled and the aqueous layer saturated with sodium chloride. The layers were separated, the organic layer dried (MgSO4) and evaporated under reduced pressure to give a quantitative yield of 2,2-dicyclopropylethanol which was pure by GC. (The product could also be distilled, b.p. 99° C./25 mm.)

Provenance & Evidence