Sodium Carbonate → Beta-citronellol, (S)-

HRID 1019344

Reaction equation

HRID 1019344 reaction equation
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][C@H:7]([CH2:9][CH:10]=[O:11])[CH3:8])[CH3:3].C(=O)([O-])[O-].[Na+].[Na+].[H][H]>[Cr].[Cu]>[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][C@@H:7]([CH2:9][CH2:10][OH:11])[CH3:8])[CH3:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 754276-Octenal, 3,7-dimethyl-, (3R)-HCID 178418361HCID 178418361, compound2×

Product 1

HCID 7793Beta-citronellol, (S)-Yield 73%

Reagents, catalysts & solvents 1

HCID 9833946Chromium, compd. with copper (1:1)Catalyst

Procedure

Into a 100-ml autoclave were introduced 20.5 g (132.8 mmol) of (R)-citronellal, 1.0 g (5%, wt/wt) of a copper-chromium catalyst, and 0.04 g (0.2%, wt/wt) of sodium carbonate. After the atmosphere in the system was replaced with hydrogen, the reaction mixture was vigorously agitated in a hydrogen atmosphere (3.4 MPa) at 130° C. for 4.5 hours and then cooled. Thereafter, the catalyst was removed by filtration. The crude citronellol obtained was distilled under reduced pressure (70° C./1,870 Pa) to obtain 15.15 g of (S) -citronellol. Yield, 73%. Purity, 98.6% (of which α-citronellol accounted for 3.4%).

Workup

  1. temperaturecooled
  2. customThereafter, the catalyst was removed by filtration
  3. customThe crude citronellol obtained
  4. distillationwas distilled under reduced pressure (70° C./1,870 Pa)

Sources & evidence

ORD record
ord-8854cd3a74a645768becf2b38a64d59e
Source dataset
uspto-grants-2002_11
Patent number
US06486353B2

Linked notes

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