Oxygen → D-Citronellol

HRID 1735518Notes

Reaction equation

HRID 1735518 reaction equation
O=O.[CH3:3][C:4](=[CH:6][CH2:7][CH2:8]/[C:9](=[CH:11]/[CH2:12][OH:13])/[CH3:10])[CH3:5].C(OCC)(=O)C>O>[CH3:3][C:4](=[CH:6][CH2:7][CH2:8][C@H:9]([CH2:11][CH2:12][OH:13])[CH3:10])[CH3:5]

Participants

5

Reactant 3

HCID 977OxygenHCID 8857Ethyl AcetateHCID 637566Geraniol

Product 1

HCID 101977D-CitronellolYield 86.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A 185 ml autoclave was charged in a glove box (O2 content<1 ppm) with 8.8 g geraniol VIII [(E)-3,7-dimethyl-2,6-octadien-1-ol], 75.2 mg ((S)-MeO-BIPHEP-TS-Na)Ru(OCOCF3)2, 31 ml ethyl acetate and 8 ml water. The hydrogenation was effected under vigorous stirring at 20 ° C. and 60 bar. After 68 hours the conversion amounted to 96%. The organic phase was separated and evaporated at 45 ° C./17 mbar. The residue consisted 92% (R)-Citronellol (A) and 4% by-product B. For purification the clear residue was destilled at 60° C./0.2 mbar. There were obtained 7.7 g (R)-Citronellol (A) [(R)-3,7-dimethyl-6-octen-1-ol] as a colourless oil; e.e. 97%.

Workup

  1. customThe organic phase was separated
  2. customevaporated at 45 ° C./17 mbar
  3. customFor purification the clear residue
  4. customwas destilled at 60° C.

Sources & evidence

ORD record
ord-805cacc6df6448e7be5b3d22aa9a862a
Source dataset
uspto-grants-1996_07
Patent number
US05536858

Reaction notes

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