Rac. benzyl 2,6,10-trimethylundeca-4,8-dien-1yl ether → 2,6,10-Trimethylundecan-1-ol

HRID 1277536Notes

Reaction equation

HRID 1277536 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

HCID 70572593Rac. benzyl 2,6,10-trimethylundeca-4,8-dien-1yl etherHCID 178418361HCID 178418361, compound

Product 1

HCID 125714642,6,10-Trimethylundecan-1-olYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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.).

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe oily residue was dissolved in 10 ml
  4. filtrationThe catalyst was again filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. distillationThe residue wasevaporatively distilled

Sources & evidence

ORD record
ord-338e1aaaed5647cc955363a97ce22c34
Source dataset
uspto-grants-1981_07
Patent number
US04277610

Reaction notes

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