Acetone → 6,10-Dimethylundecan-2-one

HRID 1655097Notes

Reaction equation

HRID 1655097 reaction equation
[CH3:1][C:2]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])=[CH:3][CH:4]=[CH:5][C:6](=[O:8])[CH3:7].CC(C)=CCC/C(/C)=C/C=C/C(C)=O.CC(=CCCC(=CC=O)C)C.CC(C)=O>[Pd].C(O)C>[CH3:1][CH:2]([CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:3][CH2:4][CH2:5][C:6](=[O:8])[CH3:7]

Participants

7

Reactant 4

HCID 180AcetoneHCID 88433,7-Dimethylocta-2,6-DienalHCID 78954(3E,5E)-6,10-dimethyl-2-undeca-3,5,9-trienoneHCID 17570033E,5E-Pseudoionone

Product 1

HCID 954956,10-Dimethylundecan-2-oneYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 17.82 g (92.8 mmoles) of 6,10-dimethyl-3,5,9-undecatrien-2-one ("pseudoionone", prepared from citral and acetone as described by A. Russell, et al., Organic Syntheses, Collective Volume-3, pages 747-750) and 1.0 g of 5% palladium on activated carbon in 50 mL of absolute ethyl alcohol was shaken vigorously under a hydrogen atmosphere (approximately 2-3 atm. pressure) for 30 minutes. After removal of the catalyst by filtration through a small pad of Hyflo Super-Cel® filtering aid, the filtrate was diluted with 150 mL of hexane. The organic layer was subsequently washed with water (2×400 mL), then dried over anhydrous magnesium sulfate, and re-filtered. Removal of the hexane by evaporation at reduced pressure, followed by distillation, afforded 15.95 g (87% yield) of 6,10-dimethyl-2-undecanone: boiling point 68°-72° C. at 0.15 mm. A previous synthesis of the latter ketone has been reported by F. G. Fischer, et al., Ann., 475, 183 (1929).

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration through a small pad of Hyflo Super-Cel®
  3. filtrationfiltering aid
  4. additionthe filtrate was diluted with 150 mL of hexane
  5. washThe organic layer was subsequently washed with water (2×400 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationre-filtered
  8. customRemoval of the hexane
  9. customby evaporation at reduced pressure
  10. distillationfollowed by distillation

Sources & evidence

ORD record
ord-193e97be710d4574963e646131db0f03
Source dataset
uspto-grants-1995_04
Patent number
US05410094

Reaction notes

Loading…