1-(5,5-Dimethylcyclohex-1-en-1-yl)ethan-1-one → HCID 20569421, compound

A solution of 1-(5′,5′-dimethylcyclohex-1′-enyl)ethanone (13.1 g, 85.8 mmol) in Et2O (50 ml) was added dropwise with stirring within 50 min. to a suspension of LAH (895 mg, 23.6 mmol) in Et2O (150 ml). The reaction mixture was refluxed for 1 h prior to quenching at 0° C. by careful addition of water (50 ml) followed by 5 N aq. HCl (50 ml). The organic layer was separated and the aqueous one extracted with Et2O. The combined ethereal solutions were washed with water and brine, dried (Na2SO4), and concentrated in a rotary evaporator. Silica-gel FC (pentane/Et2O, 9:1, Rf=0.14) of the resulting residue (14.7 g) gave 11.2 g (85%) of 1-(5′,5′-dimethylcyclohex-1′-enyl)ethanol.

1. temperatureThe reaction mixture was refluxed for 1 h
2. customto quenching at 0° C. by careful addition of water (50 ml)
3. customThe organic layer was separated
4. extractionthe aqueous one extracted with Et2O
5. washThe combined ethereal solutions were washed with water and brine
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated in a rotary evaporator

ORD record

ord-aaf271fcf2e345e0aff63f8e9b08bf0c

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07393822B2