cis-5-Octenal → 5-Octen-1-ol, (5Z)-

Temperature

80 °C

(Z)-oct-5-enal (63 g, 0.5 mol.), heptane (63 g, 100 wt. %, technical grade), and (ethylenediamine)[1,2-bis(diphenylphosphino)ethane]ruthenium[bis((adamantane-1-carboxylate)] (45.9 mg, 0.05 mmol, 0.01 mol.%) were loaded altogether in a 300 ml 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 20 bars hydrogen. It was then heated to 80° C. and hydrogen pressure was maintained to 20 bars during all the reaction to afford desired product with 95% selectivity. After complete reaction conversion (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 initial flash distillation and further fractional distillation, (Z)-oct-5-en-1-ol was obtained in 90% yield.

1. customequipped with a mechanical stirring device
2. customSealed autoclave
3. customwas then purged
4. temperaturehydrogen pressure was maintained to 20 bars during all
5. customthe reaction

ORD record

ord-bfd43d7795134199ad31266b449cd89a

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09090534B2