Phytol → Dihydrophytol

HRID 1910407Notes

Reaction equation

HRID 1910407 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]>[Ni].C(O)C>[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

4

Reactant 1

HCID 5280435Phytol

Product 1

HCID 102459DihydrophytolYield 97%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution containing 50 g (169 mmol) of phytol (3,7,11,15-tetramethyl-hexadec-2-en-1-ol, 97% mixture of isomers) and 200 ml ethanol, reaction catalysis Raney nickel (5 g, 50% slurry in water) was added. After stirring the mixture under hydrogen atmosphere (15 psi) for 2 days, the catalyst was removed by vacuum filtration several times through the combination layers of silica and Celite bed on the top. The filtrate was concentrated under reduced pressure to give phytanol (48.8 g, 97.0%) as a colourless oil. 1H NMR in CDCl3: δ0.83, 0.85, 0.86, 0.88, 0.91 (5s, each 3H, CH3), 0.94-1.71 (m, 25H, 10CH2+4CH+OH), 3.58-3.78 (m, 2H, CH2OH).

Workup

  1. additionTo a solution containing
  2. additionwas added
  3. customthe catalyst was removed by vacuum filtration several times through the combination layers of silica and Celite bed on the top
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3b803001fb414751b5b4a5a194067710
Source dataset
uspto-grants-2013_12
Patent number
US08603999B2

Reaction notes

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