Binap, (A+-)- → D-Citronellol

HRID 2234276Notes

Reaction equation

HRID 2234276 reaction equation
C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:47][C:48](=[CH:50][CH2:51][CH2:52]/[C:53](=[CH:55]/[CH2:56][OH:57])/[CH3:54])[CH3:49].[H][H]>CO>[CH3:47][C:48](=[CH:50][CH2:51][CH2:52][C@H:53]([CH2:55][CH2:56][OH:57])[CH3:54])[CH3:49]

Participants

5

Reactant 3

HCID 634876Binap, (A+-)-HCID 637566GeraniolHCID 178418361HCID 178418361, compound

Product 1

HCID 101977D-CitronellolYield 97.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Under an inert gas atmosphere, 2.4 mg of [RuCl2(C6H6)]2 (corresponding to 0.01 μmol of Ru) were dissolved in 75 ml of methanol, 6.0 mg (80.01 μmol) of (S)-BINAP were added and the mixture was stirred for 12 h at room temperature until the resulting solution was clear. The catalyst solution was transferred to an autoclave fitted with a gas dispersion stirrer and a further 75 ml of methanol and 14.8 g of geraniol (0.096 mol, purity 95%) were added. The mixture was stirred for 24 h at a hydrogen pressure of 100 bar and a temperature of 40° C. A conversion of 98.3% was then determined by gas chromatography. A yield of 97.2% of (R)-citronellol with an enantiomeric purity of 95.2% ee was obtained.

Workup

  1. customfitted with a gas dispersion stirrer
  2. customa temperature of 40° C

Sources & evidence

ORD record
ord-f38ca3e1475a40de908b0c2630082a85
Source dataset
uspto-grants-2010_05
Patent number
US07709688B2

Reaction notes

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