4,6,6-Trimethyl-1,3-cyclohexadiene-1-carboxaldehyde → 4,6,6-Trimethylcyclohex-1-ene-1-carbaldehyde

HRID 566851Notes

Reaction equation

HRID 566851 reaction equation
[CH3:1][C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[C:5]([CH:10]=[O:11])=[CH:4][CH:3]=1>[Pd].C(O)C>[CH3:1][CH:2]1[CH2:7][C:6]([CH3:8])([CH3:9])[C:5]([CH:10]=[O:11])=[CH:4][CH2:3]1

Participants

4

Reactant 1

HCID 109206834,6,6-Trimethyl-1,3-cyclohexadiene-1-carboxaldehyde

Product 1

HCID 212637424,6,6-Trimethylcyclohex-1-ene-1-carbaldehydeYield 87.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4,6,6-trimethyl-1,3-cyclohexadiene-1-carbaldehyde (141 g, 0.94 mole), ethanol (1 l) and palladium on charcoal (10%, 0.5 g) was hydrogenated by shaking under a H2-atmosphere for 3.5 h. The H2-consumption was 23.5 l. After filtration and concentration of the thus-obtained solution, the residue was distilled at 50°/0.7 hPa, to obtain 125.3 g (87.6%) of the desired product.

Workup

  1. customThe H2-consumption
  2. filtrationAfter filtration and concentration of the thus-obtained solution
  3. distillationthe residue was distilled at 50°/0.7 hPa

Sources & evidence

ORD record
ord-071cb5a54c664502af8d9fd83f1f54ec
Source dataset
uspto-grants-2001_01
Patent number
US06177400B1

Reaction notes

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