1-(5,5-Dimethylcyclohex-1-en-1-yl)ethan-1-one → HCID 20569421, compound
Reaction equation
[CH3:1][C:2]([C:4]1[CH2:9][C:8]([CH3:11])([CH3:10])[CH2:7][CH2:6][CH:5]=1)=[O:3].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH3:1][CH:2]([OH:3])[C:4]1[CH2:9][C:8]([CH3:11])([CH3:10])[CH2:7][CH2:6][CH:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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.