Oxygen → D-Citronellol

HRID 440174Notes

Reaction equation

HRID 440174 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 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 500 ml autoclave was charged in a glove box (O2 content <1 pm) with 27.0 g (175.0 mmol) of geraniol, 36 ml of methanol and 100 ml of catalyst solution prepared according to Example 6. The hydrogenation was carried out at 20° C., a constant pressure of 60 bar of H2 and while stirring intensively. The conversion was 100% after 22 hours. The pale yellow hydrogenation solution was flushed from the autoclave and evaporated on a rotary evaporator at 60°/17 mbar. The residue was distilled at 65°/0.01 mbar. 26.7 g (99.0%) of (R)-citronellol were obtained as a colourless oil, with an enantiomeric purity of 74.3% e.e.. The determination of the e.e. value was effected by GC analysis of the diastereomeric ester prepared with Trolox™ methyl ether.

Workup

  1. customprepared
  2. customwas carried out at 20° C.
  3. customafter 22 hours
  4. customThe pale yellow hydrogenation solution was flushed from the autoclave
  5. customevaporated on a rotary evaporator at 60°/17 mbar
  6. distillationThe residue was distilled at 65°/0.01 mbar

Sources & evidence

ORD record
ord-76a91760e61d47d8bd7ae7041c6c1e47
Source dataset
uspto-grants-1996_05
Patent number
US05516944

Reaction notes

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