Oxygen → D-Citronellol

Participants

Reaction Steps

A 500 ml autoclave was charged in a glove box (O2 content <1 ppm) with 27.0 g (175.0 mmol) of geraniol and 36 ml of methanol. To this solution was added a catalyst solution prepared by dissolving 6.35 mg (0.0073 mmol) of [Ru(COD)(CF3COO)2 ]2 and 10.25 mg (0.0146 mmol) of (S)-(MeO)3BIPHEP in 100 ml of methanol at room temperature and while stirring for 16 hours. The hydrogenation was effected at 20° C. and 60 bar. The conversion after 1 hour amounted to 100.0%. The hydrogenation solution was evaporated at 45° C./17 mbar and the crude product was distilled at 60°-65° C./0.03 mbar. There were obtained 26.8 g of (R)-citronellol as a colourless oil; e.e. 98.8%.

Provenance & Evidence