Hydrogen Peroxide → (6,6-Dimethylbicyclo[3.1.1]heptan-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

(+)-β-pinene (113) (36.6 g; 0.27 mol) was dissolved in THF (100 ml) and cooled down to 0° C. BH3.DMS in THF (2 M; 47.3 ml) was added drop wise. The reaction mixture was stirred for 0.5 h. Ethanol (90 ml) was added. 1 M NaOH (aq) (95 ml) was added. The reaction mixture was cooled to 0° C. 33 ml 30% H2O2 was added drop wise while the temperature was not allowed to rise above 35° C. The reaction mixture was refluxed for 1 h and poured into water (1 l). The solution was extracted with TBME. The combined organic layers were washed with water and brine, dried over Na2SO4 and evaporated to dryness. Remaining α-pinene was distilled off using Kugelrohr distillation (8-12 mbar; 50-60° C.), giving 38.6 g (0.25 mol, yield=93%) of (+)-cis-myrtanol (14) as a colourless oil.

Provenance & Evidence