2-(2-Formylethyl)-3-isopropenyl-1-methyl-cyclopent-1-ene → 2-(2-Formylethyl)-3-isopropyl-1-methyl-cyclopent-1-ene

HRID 437485Notes

Reaction equation

HRID 437485 reaction equation
[CH:1]([CH2:3][CH2:4][C:5]1[CH:9]([C:10]([CH3:12])=[CH2:11])[CH2:8][CH2:7][C:6]=1[CH3:13])=[O:2].[H][H]>C(OCC)(=O)C.[Pd]>[CH:1]([CH2:3][CH2:4][C:5]1[CH:9]([CH:10]([CH3:11])[CH3:12])[CH2:8][CH2:7][C:6]=1[CH3:13])=[O:2]

Participants

5

Reactant 2

HCID 124807202-(2-Formylethyl)-3-isopropenyl-1-methyl-cyclopent-1-eneHCID 178418361HCID 178418361, compound

Product 1

HCID 124807212-(2-Formylethyl)-3-isopropyl-1-methyl-cyclopent-1-ene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3.6 g of 2-(2-formylethyl)-3-isopropenyl-1-methyl-cyclopent-1-ene were hydrogented in 80 ml of ethyl acetate in the presence of 500 mg of palladium on calcium carbonate (5%). After the uptake of one equivalent of hydrogen, the solution was filtered over Celite, concentrated and subjected under a high vacuum to a short-path distillation. 2-(2-Formylethyl)-3-isopropyl-1-methyl-cyclopent-1-ene having a fresh, woody fragrance was obtained in quantitative yield; boiling point 0.001 about 70° C; nD20 = 1.4703; IRfilm : νmax = 2740, 1728, 1470, 1385, 1368 and 1100 cm-1.

Workup

  1. concentrationconcentrated
  2. distillationsubjected under a high vacuum to a short-path distillation

Sources & evidence

ORD record
ord-5f286fcef22f4c6e8022d52fd505e141
Source dataset
uspto-grants-1977_06
Patent number
US04031132

Reaction notes

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