Oxygen → D-Citronellol

HRID 327848Notes

Reaction equation

HRID 327848 reaction equation
O=O.[CH3:3]/[C:4](/[CH2:8][CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])=[CH:5]\[CH2:6][OH:7]>CO>[CH3:3][C@H:4]([CH2:8][CH2:9][CH:10]=[C:11]([CH3:12])[CH3:13])[CH2:5][CH2:6][OH:7]

Participants

4

Reactant 2

HCID 977OxygenHCID 637566Geraniol

Product 1

HCID 101977D-CitronellolYield 97.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 500 ml autoclave was charged in a glove box (O2 content <1 ppm) with 24.0 g (155.6 mmol) of (E)-3,7-dimethylocta-2,6-dien-1-ol, 22 ml of methanol and 100 ml of catalyst solution. This mixture was hydrogenated at 20°, a constant pressure of 60 bar H2 and while stirring intensively. The conversion was 100% after 48 hours. The pale yellow hydrogenation solution was rinsed from the autoclave and evaporated on a rotary evaporator at 60°/17 mbar. The residue was distilled at 65%/0.01 mbar. There were obtained 23.8 g of (R)-3,7-dimethyloct-6-en-1-ol as a colourless oil with an enantiomeric purity of 98.4% e.e.

Workup

  1. customwas hydrogenated at 20°
  2. customafter 48 hours
  3. washThe pale yellow hydrogenation solution was rinsed from the autoclave
  4. customevaporated on a rotary evaporator at 60°/17 mbar
  5. distillationThe residue was distilled at 65%/0.01 mbar

Sources & evidence

ORD record
ord-cae1d4525e704aeba4600f74df37919c
Source dataset
uspto-grants-1993_12
Patent number
US05274125

Reaction notes

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