Tetrahydrofuran → 4-Phenylcyclohexanol
Reaction equation
[C:1]1([CH:7]([CH2:12][CH3:13])[CH2:8][C:9](=O)[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:20]1CCCC1>>[C:1]1([CH:7]2[CH2:12][CH2:13][CH:10]([OH:20])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
4
Procedure
4-Phenylhexanone (1.74 g; 10 mmoL) is mixed with 1M lithium aluminum hydride (LiAlH4) solution in tetrahydrofuran (THF) (10 mL; 10 mmoL). The reaction mixture is stirred and refluxed for 6 hrs. After the starting ketone is consumed as determined by thin-layer chromatography (TLC) and gas phase chromatography (GC), the reaction mixture is carefully quenched with water (40 mL) whereupon a precipitate forms. Then, hydrochloric acid (10 mL) is added to dissolve the precipitate, and the solution is twice extracted with diethyl ether (20 mL twice). The combined ether portions are dried with Na2SO4, and the solvent is evaporated to yield 4-phenylcyclohexanol (1.71 g; 74%). The purity and identity of the compound are established by TLC and GC using an authentic sample of the material obtained from Lancaster Company.