4,6,6-Trimethyl-1,3-cyclohexadiene-1-carboxaldehyde → 2,2,4-Trimethyl-1-cyclohexanecarbaldehyde

HRID 566852Notes

Reaction equation

HRID 566852 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(OCC)(=O)C>[CH3:9][C:6]1([CH3:8])[CH2:7][CH:2]([CH3:1])[CH2:3][CH2:4][CH:5]1[CH:10]=[O:11]

Participants

4

Reactant 1

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

Product 1

HCID 212637402,2,4-Trimethyl-1-cyclohexanecarbaldehydeYield 67.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4,6,6-Trimethyl-1,3-cyclohexadiene-1-carbaldehyde (100.0 g, 0.66 mole), 11 of ethyl acetate and 0.3 g of palladium on charcoal (0.3 g) were hydrogenated as described in Example 1, over 3 days. The H2-consumption was 35 1. The mixture was then heated with pyridin chlorochromate to oxidize the amounts of alcohol formed. After filtration and concentration, the product was distilled at 65-73°/18 hPa, to obtain 68.8 g (67%) of the desired product in the form of a mixture of 2 isomers in a ratio of 1:3.

Workup

  1. customThe H2-consumption
  2. temperatureThe mixture was then heated with pyridin chlorochromate
  3. customformed
  4. filtrationAfter filtration and concentration
  5. distillationthe product was distilled at 65-73°/18 hPa

Sources & evidence

ORD record
ord-2fe1bbd9d3ea49afba3e5b8061ff739f
Source dataset
uspto-grants-2001_01
Patent number
US06177400B1

Reaction notes

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