Phytol → Dihydrophytol

HRID 1261869Notes

Reaction equation

HRID 1261869 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]>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][CH:7]([CH2:9][CH2:10][CH2:11][CH:12]([CH2:14][CH2:15][CH2:16][CH:17]([CH2:19][CH2:20][OH:21])[CH3:18])[CH3:13])[CH3:8])[CH3:1]

Participants

5

Reactant 2

HCID 5280435PhytolHCID 178418361HCID 178418361, compound

Product 1

HCID 102459Dihydrophytol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Phytol (200.45 g) was hydrogenated at room temperature in ethanol (1 lit) with 30% slurry of Raney Nickel (85.7 g), with a stream of hydrogen for 104 hours to get dihydrophytol, 201.87 g (100%). Mass spec: m/z 297 (M−1)+. 1H NMR (CDCl3), δ ppm: 0.83-0.88 (m, 15H), 1.04-1.53 (m, 24H), 1.75 (s), 3.60-3.71 (m 2H). This product is used without further purification in the conversion to the corresponding bromide.

Sources & evidence

ORD record
ord-fdec45f3431548e2bbabf782d7fdbab4
Source dataset
uspto-grants-2013_06
Patent number
US08471035B1

Reaction notes

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