Triethylamine → Dihydrophytol

HRID 2304130Notes

Reaction equation

HRID 2304130 reaction equation
[CH3:1][C:2]([CH2:6][CH2:7][CH2:8][CH:9]([CH3:21])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:20])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[CH:3][CH2:4][OH:5].C(N(CC)CC)C.[H][H]>C(O)C.[Pd]>[CH3:1][CH:2]([CH2:6][CH2:7][CH2:8][CH:9]([CH3:21])[CH2:10][CH2:11][CH2:12][CH:13]([CH3:20])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:3][CH2:4][OH:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1453863,7,11,15-Tetramethylhexadec-2-en-1-olHCID 178418361HCID 178418361, compound

Product 1

HCID 102459DihydrophytolYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 50.0 g (169 mmol) of 3,7,11,15-tetramethyl-2-hexadecen-1-ol in 200 mL of ethanol were added 0.3 g (3 mmol) of triethylamine and 500 mg of 5% Pd on carbon. The mixture was maintained under 50 psi (345 kPa) of hydrogen on a Parr hydrogenator for 24 h. The mixture was filtered and concentrated, and distillation afforded 41.7 g (83%) of 3,7,11,15-tetramethyl-1-hexadecanol as a clear, colorless liquid, bp 150-155° C. at 0.05 mm Hg.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. distillationdistillation

Sources & evidence

ORD record
ord-ddf495c639a2488abde974ff1510c437
Source dataset
uspto-grants-2002_08
Patent number
US06433359B1

Reaction notes

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