Phytol → Dihydrophytol

HRID 2228413Notes

Reaction equation

HRID 2228413 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([CH2:9][CH2:10][CH2:11][C@H:12]([CH2:14][CH2:15][CH2:16]/[C:17](=[CH:19]/[CH2:20][OH:21])/[CH3:18])[CH3:13])[CH3:8])[CH3:3].[H][H]>C(O)C.[Ni]>[CH2:20]([OH:21])[CH2:19][CH:17]([CH2:16][CH2:15][CH2:14][CH:12]([CH2:11][CH2:10][CH2:9][CH:7]([CH2:6][CH2:5][CH2:4][CH:2]([CH3:3])[CH3:1])[CH3:8])[CH3:13])[CH3:18]

Participants

5

Reactant 2

HCID 5280435PhytolHCID 178418361HCID 178418361, compound

Product 1

HCID 102459DihydrophytolYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of phytol (49.3 g, 166 mmol) in ethanol (250 ml) was reduced with hydrogen gas at atmospheric pressure over Raney nickel for 3 days. The catalyst was removed by filtration through Celite® and the filtrate concentrated under reduced pressure to give phytanol (49.3 g, 100%). 1H-n.m.r. (CDCl3) δ0.8-0.95 (m, 15H), 1.0-1.75 (m, 24H), 3.65-3.75 (m, 2H). 13C-n.m.r. (CDCl3) δ19.67 (3×Me), 22.60 (Me), 22.69 (Me), 24.36 (CH2), 24.45 (CH2), 24.78 (CH2), 27.95 (CH), 29.50 (CH), 32.76 (2×CH), 37.28-37.43 (m, 5×CH2), 39.35 (CH2), 39.73 and 40.05 (together CH2), 61.18 (CH2).

Workup

  1. customThe catalyst was removed by filtration through Celite®
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-b879bcd893594e1cbb28ceafc67156ae
Source dataset
uspto-grants-2002_07
Patent number
US06417009B1

Reaction notes

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