Oxygen → D-Citronellol

HRID 376089Notes

Reaction equation

HRID 376089 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]>CO>[CH3:3][C:4](=[CH:6][CH2:7][CH2:8][C@H:9]([CH2:11][CH2:12][OH:13])[CH3:10])[CH3:5]

Participants

4

Reactant 2

HCID 977OxygenHCID 637566Geraniol

Product 1

HCID 101977D-CitronellolYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 500 ml autoclave was charged in a glove box (O2 content <1 ppm) with 27.0 g (175.0 mmol) of geraniol, 136 ml of methanol and 3.6 mg of Ru(CF3COO)2 [(S)-(MeO)3BIPHEP] as the catalyst. The hydrogenation was effected at 20° C. and 60 bar. The conversion after 23 hours amounted to 89.4%. The hydrogenation solution was evaporated at 45° C./17 mbar and the crude product was distilled at 60°-65° C./0.03 mbar. There were obtained 26.4 g of (R)-citronellol, which still contained 10.6% of unreacted geraniol, as a colourless oil; e.e. 98.9%.

Workup

  1. customwas effected at 20° C.
  2. customThe hydrogenation solution was evaporated at 45° C./17 mbar
  3. distillationthe crude product was distilled at 60°-65° C./0.03 mbar

Sources & evidence

ORD record
ord-bc4ce4799fe3428695dd0e4aee2f15f5
Source dataset
uspto-grants-1996_01
Patent number
US05488172

Reaction notes

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