4-(5-Isopropenyl-2-methyl-1-cyclopenten-1-yl)-2-butanone → 3-Isopropyl-1-methyl-2-(3-oxobutyl)-cyclopent-1-ene

HRID 1658174Notes

Reaction equation

HRID 1658174 reaction equation
[C:1]([CH:4]1[CH2:8][CH2:7][C:6]([CH3:9])=[C:5]1[CH2:10][CH2:11][C:12](=[O:14])[CH3:13])([CH3:3])=[CH2:2].[H][H]>C(OCC)(=O)C.[Pd]>[CH:1]([CH:4]1[CH2:8][CH2:7][C:6]([CH3:9])=[C:5]1[CH2:10][CH2:11][C:12](=[O:14])[CH3:13])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 37756924-(5-Isopropenyl-2-methyl-1-cyclopenten-1-yl)-2-butanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 213885343-Isopropyl-1-methyl-2-(3-oxobutyl)-cyclopent-1-eneYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4 g of 3-isopropenyl-1-methyl-2-(3-oxobutyl)-cyclopent-1-ene were hydrogenated in 50 ml of ethyl acetate in the presence of 400 mg of palladium on calcium carbonate (5%). After the uptake of one equivalent of hydrogen, the solution was filtered over Celite, concentrated and distilled under a high vacuum. There were obtained 4 g of 3-isopropyl-1-methyl-2-(3-oxobutyl)-cyclopent-1-ene; boiling point 0.005 about 70°C; nD20 = 1.4709; IRfilm : μmax = 1725, 1390/70 and 1170 cm-1. The compound has a woody, floral note.

Workup

  1. concentrationconcentrated
  2. distillationdistilled under a high vacuum

Sources & evidence

ORD record
ord-7a71dc3b5a5a42c6a21c6cd4e9216120
Source dataset
uspto-grants-1976_06
Patent number
US03963675

Reaction notes

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