Benzene hexane → Dihydrophytol

HRID 235802

Reaction equation

HRID 235802 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].C1C=CC=CC=1.CCCCCC>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

6

Reactant 3

HCID 110624Benzene hexaneHCID 5280435PhytolHCID 178418361HCID 178418361, compound

Product 1

HCID 102459DihydrophytolYield 82.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

Phytol (30.0 g, 0.101 mol) was dissolved in 200 ml of ethanol. A suspension of 1.8 g of Raney-Ni (W-1) in 5 ml of ethanol was added thereto, and hydrogenation was carried out under hydrogen for about 5 hours so that 2405 ml of hydrogen (theoretical volume at 24° C.; 2465 ml) was absorbed. After filtering off the catalyst through a filter paper, the ethanol was evaporated. Yield 29.9 g. Silica gel column chromatography with benzene-hexane (1:1) gave 24.7 g of the title compound (yield 82.3%).

Workup

  1. additionwas added
  2. customwas absorbed
  3. filtrationAfter filtering off the catalyst through a filter paper
  4. customthe ethanol was evaporated

Sources & evidence

ORD record
ord-d5313b1b216e487a92dd93cc260a0033
Source dataset
uspto-grants-1987_02
Patent number
US04642314

Linked notes

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