Rac. benzyl 2,6,10-trimethylundeca-4,8-dien-1yl ether → 2,6,10-Trimethylundecan-1-ol
Reaction equation
[CH3:1][CH:2]([CH2:12][CH:13]=[CH:14][CH:15]([CH3:22])[CH2:16][CH:17]=[CH:18][CH:19]([CH3:21])[CH3:20])[CH2:3][O:4]CC1C=CC=CC=1.[H][H]>C(OCC)(=O)C>[CH3:1][CH:2]([CH2:12][CH2:13][CH2:14][CH:15]([CH3:22])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:3][OH:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 0.15 g (0.5 mmole) of rac. benzyl 2,6,10-trimethylundeca-4,8-dien-1yl ether, 0.1 g of 5% by weight palladiumon 95% by weight carbon and 10 ml. of ethyl acetate was stirred in an atmosphere of hydrogen for 16 hours at room temperature. The catalyst was filtered and the filtrate was concentrated in vacuo. The oily residue was dissolved in 10 ml. of ethyl acetate and rehydrogenated over 0.1 g of 5% palladium on carbon, for 5 hours at room temperature. The catalyst was again filtered and the filtrate was concentrated in vacuo. The residue wasevaporatively distilled giving 0.092 g (86%) of rac. 2,6,10-trimethylundecan-1-ol as a colorless oil, b.p. 100°-105° C. (bath temperature) (0.02 mm Hg.).