6-oxoheptanal → 7-hydroxyheptan-2-one

Temperature

90 °C

6-oxoheptanal (12.8 g, 0.1 mol.), toluene (76.8 g, 600 wt. %) and (ethylenediamine)[1,2-bis(diphenylphosphino)ethane]ruthenium (bispivalate) (9.6 mg, 0.0125 mmol, 0.0125 mol.%) were loaded altogether in a 200 ml autoclave equipped with a mechanical stirring device. Sealed autoclave was then purged under stirring with nitrogen (3 times to 5 bars) and hydrogen (3 times 5 bars) before being pressurized to 20 bars hydrogen. It was then heated to 90° C. and hydrogen pressure was maintained to 50 bars during all the reaction to afford desired product with 94% selectivity. Upon reaction completion (checked by both hydrogen consumption and GC), autoclave was then 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 chromatography, 7-hydroxyheptan-2-one 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 50 bars during all
5. customthe reaction

ORD record

ord-c7f14b11a5f64910a783dca6baeece78

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09090534B2