Citronellal → Citronellol

Temperature

90 °C

3,7-dimethyloct-6-enal (154 g, 1 mol.), heptane (154 g, 100 wt. %, technical grade) and (ethylenediamine)[1,2-bis(diphenylphosphino) ethane]ruthenium(bisbenzoate) (26.5 mg, 0.033 mmol, 0.0033 mol.%) were loaded altogether in a 11 autoclave equipped with a mechanical stirring device. Sealed autoclave was then purged under stirring with nitrogen (3 times 5 bars) and hydrogen (3 times 5 bars) before being pressurized to 30 bars hydrogen. It was then heated to 90° C. and hydrogen pressure was maintained to 30 bars during all the reaction to afford desired product with 99% selectivity. Upon reaction completion (checked by both hydrogen consumption and GC), autoclave was cooled down to 25° C. It was then depressurized and purged with nitrogen (3 times 5 bars) and reaction mixture was then transferred to a round-bottomed flask and solvent was removed under vacuum. After flash distillation, pure 3,7-trimethyloct-6-en-1-ol was obtained in 98% yield.

1. customequipped with a mechanical stirring device
2. customSealed autoclave
3. customwas then purged
4. temperaturehydrogen pressure was maintained to 30 bars during all
5. customthe reaction

ORD record

ord-46d7b0af5c6848f0a90468173d30a3b8

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09090534B2