Ethanone, 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)- → (1S-cis)-1-(2,2,6-Trimethylcyclohexyl)ethanone

HRID 2420134Notes

Reaction equation

HRID 2420134 reaction equation
[C:1]([CH:4]1[CH:9]([CH3:10])[CH:8]=[CH:7][CH2:6][C:5]1([CH3:12])[CH3:11])(=[O:3])[CH3:2]>C(O)C.[Pd]>[C:1]([C@H:4]1[C@@H:9]([CH3:10])[CH2:8][CH2:7][CH2:6][C:5]1([CH3:11])[CH3:12])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 117287Ethanone, 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-

Product 1

HCID 6452676(1S-cis)-1-(2,2,6-Trimethylcyclohexyl)ethanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

464 g 1-acetyl-2,2,6-trimethyl-4-cyclohexene (V, prepared according to K. S. Ayyar Chem.Comm. 1973, 161) (2.8 moles) in 800 ml of ethanol and 3 g 10% palladium on charcoal are hydrogenated in an autoclave under a pressure of 50 atm and at 50° C. After the uptake ceases, the reaction mixture is filtered and concentrated by distillation under reduced pressure. The product cis-1-acetyl-2,2,6-trimethylcyclohexane (VI, containing about 10% of the trans isomer) is collected at 83°-88° C/12 mm; yield 420 g (90%).

Workup

  1. customare hydrogenated in an autoclave under a pressure of 50 atm and at 50° C
  2. filtrationAfter the uptake ceases, the reaction mixture is filtered
  3. concentrationconcentrated by distillation under reduced pressure
  4. additionThe product cis-1-acetyl-2,2,6-trimethylcyclohexane (VI, containing about 10% of the trans isomer)
  5. customis collected at 83°-88° C/12 mm

Sources & evidence

ORD record
ord-a32fdf0c3ec843f49a9a84cc0844dadd
Source dataset
uspto-grants-1978_08
Patent number
US04109022

Reaction notes

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