Oxygen → D-Citronellol

Participants

Reaction Steps

A 500 ml autoclave was charged in a glove box (O2 content <1 pm) with 27.0 g (175.0 mmol) of geraniol, 36 ml of methanol and 100 ml of catalyst solution prepared according to Example 6. The hydrogenation was carried out at 20° C., a constant pressure of 60 bar of H2 and while stirring intensively. The conversion was 100% after 22 hours. The pale yellow hydrogenation solution was flushed from the autoclave and evaporated on a rotary evaporator at 60°/17 mbar. The residue was distilled at 65°/0.01 mbar. 26.7 g (99.0%) of (R)-citronellol were obtained as a colourless oil, with an enantiomeric purity of 74.3% e.e.. The determination of the e.e. value was effected by GC analysis of the diastereomeric ester prepared with Trolox™ methyl ether.

Provenance & Evidence