Geraniol → Citronellol

HRID 1591359Notes

Reaction equation

HRID 1591359 reaction equation
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6]/[C:7](=[CH:9]/[CH2:10][OH:11])/[CH3:8])[CH3:3].[H][H]>CO>[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][CH:7]([CH2:9][CH2:10][OH:11])[CH3:8])[CH3:3]

Participants

4

Reactant 2

HCID 637566GeraniolHCID 178418361HCID 178418361, compound

Product 1

HCID 8842CitronellolYield 97,775.102%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a 200-ml stainless steel-made autoclave were placed 16.1 g (0.104 mmole) of geraniol, 17.7 mg (0.0208 mmole) of Ru(OAc)2 ((-)-OcH-BINAP) as obtained in Example 7, and 18 ml of methanol. This mixture was stirred at a hydrogen pressure of 100 kg/cm2 and a temperature of 25° C. for 5 hours. After completion of the reaction, the solvent was removed by evaporation, and the residual crude product was subjected to vacuum distillation using a Claisen distillation flask, thereby obtaining 15.89 g of citronellol. The percent yield was 98%, and the optical purity of the citronellol was 98.3% ee.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed by evaporation
  3. distillationthe residual crude product was subjected to vacuum distillation
  4. distillationa Claisen distillation flask

Sources & evidence

ORD record
ord-3ce56434ac26404d86fe0aa4b98faa88
Source dataset
uspto-grants-1993_04
Patent number
US05206399

Reaction notes

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