3-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl- → 2,2,3-Trimethylcyclopentaneacetaldehyde

HRID 1975630Notes

Reaction equation

HRID 1975630 reaction equation
[CH3:1][C:2]1[C:6]([CH3:8])([CH3:7])[CH:5]([CH2:9][CH:10]=[O:11])[CH2:4][CH:3]=1.[H][H]>[Pd]>[CH3:8][C:6]1([CH3:7])[CH:2]([CH3:1])[CH2:3][CH2:4][CH:5]1[CH2:9][CH:10]=[O:11]

Participants

4

Reactant 2

HCID 984973-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl-HCID 178418361HCID 178418361, compound

Product 1

HCID 224142552,2,3-TrimethylcyclopentaneacetaldehydeYield 90.7%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
80 °C

Procedure

A three liter autoclave with a stirrer is charged with 830 g of campholenic aldehyde and 56 g of catalyst Pd(5%)/C. Hydrogen is introduced until the pressure reaches 30 bars. The mixture is heated up to 80° C. with stirring for five hours. The calculated amount of hydrogen is now absorbed. The catalyst is separated by filtration and washed with ethanol. The solvent is removed by vacuum evaporation and 815 g of crude saturated aldehyde are obtained (purity: 95%, GC). The vacuum distillation of the crude through a Widmer column gives 763 g of pure product (purity 95%); bp20 85° C.; nD20 : 1,4553;

Workup

  1. customThe calculated amount of hydrogen is now absorbed
  2. customThe catalyst is separated by filtration
  3. washwashed with ethanol
  4. customThe solvent is removed by vacuum evaporation and 815 g of crude saturated aldehyde
  5. customare obtained (purity: 95%, GC)
  6. distillationThe vacuum distillation of the crude through a Widmer column

Sources & evidence

ORD record
ord-09c1fcba6c654e019dc94b973e7802a6
Source dataset
uspto-grants-1994_02
Patent number
US05288701

Reaction notes

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