Oxygen → D-Citronellol

HRID 376086Notes

Reaction equation

HRID 376086 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 110.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 500 ml autoclave was charged in a glove box (O2 content <1 ppm) with 24.0 g (155.6 mmol) of geraniol and 20 ml of methanol. To this solution was added a catalyst solution prepared by dissolving 5.6 mg (0.0064 mmol) of [Ru(COD)(CF3COO)2 ]2 and 8.3 mg (0.0129 mmol) of (S)-(MeO)2BIPHEP in 100 ml of methanol at room temperature and stirring for 16 hours. The hydrogenation was effected at 20° C. and 60 bar. The conversion after 1 hour amounted to 99.9%. 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 26.8 g of (R)-citronellol as a colourless oil, e.e. 98.0%.

Workup

  1. additionTo this solution was added a catalyst solution
  2. customprepared
  3. customwas effected at 20° C.
  4. waitThe conversion after 1 hour amounted to 99.9%
  5. customThe hydrogenation solution was evaporated at 45° C./17 mbar
  6. distillationthe crude product was distilled at 60°-65° C./0.03 mbar

Sources & evidence

ORD record
ord-43a80c49646443b0a9a3bc28222f8952
Source dataset
uspto-grants-1996_01
Patent number
US05488172

Reaction notes

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