5-Phenyl-1-pentanol → Cyclohexanepentanol

To a portion of 100 mL glacial acetic acid, purged with argon, was added 5.62 g of PtO2 (Aldrich) followed by a solution of 25.00 g (152.2 mmol, Aldrich) of 5-phenyl-1-pentanol in 100 mL glacial acetic acid. The reaction vessel was evacuated and purged with H2 three times, the the reaction mixture was stirred under H2 (1 atm) of 22 hours. The reaction was not complete by thin layer chromatography. A second portion of 3.25 (Aldrich) of PtO2 was added and the reaction was stirred under H2 (1 atm) for an additional 32 hours. The mixture was filtered through a 0.4 μM polycarbonate filter, the filtrate was concentrated in vacuo and then azeotroped four times with toluene to give 28.08 g (164.9 mmol, 100%) of a cloudy liquid. 1H NMR indicated the crude material was about a 2:1 mixture of the alcohol title compound and the corresponding acetate.

1. customTo a portion of 100 mL glacial acetic acid, purged with argon
2. additionwas added 5.62 g of PtO2 (Aldrich)
3. customThe reaction vessel was evacuated
4. custompurged with H2 three times
5. additionA second portion of 3.25 (Aldrich) of PtO2 was added
6. stirringthe reaction was stirred under H2 (1 atm) for an additional 32 hours
7. filtrationThe mixture was filtered through a 0.4 μM polycarbonate
8. filtrationfilter
9. concentrationthe filtrate was concentrated in vacuo
10. customazeotroped four times with toluene
11. customto give 28.08 g (164.9 mmol, 100%) of a cloudy liquid

ORD record

ord-edf0c6166a164e6f89b65e816177430a

Source dataset

uspto-grants-1992_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05135939