Ethanone, 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)- → Trans-4-Acetyl-3,5,5-Trimethylcyclohexene

HRID 2416168Notes

Reaction equation

HRID 2416168 reaction equation
[CH3:1][C:2]([CH:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][CH:7]=[CH:6][CH:5]1[CH3:12])=[O:3]>O.O.O.[Rh](Cl)(Cl)Cl.C(O)C>[CH3:1][C:2]([C@@H:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][CH:7]=[CH:6][C@H:5]1[CH3:12])=[O:3]

Participants

4

Reactant 1

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

Product 1

HCID 54437493Trans-4-Acetyl-3,5,5-Trimethylcyclohexene

Reagents, catalysts & solvents 2

HCID 11459718Rhodium chloride trihydrateCatalystHCID 702EthanolSolvent

Procedure

In a 200-ml four-necked flask equipped with a thermometer, condenser and a stirrer, placed were 2,6,6-trimethyl-3-cyclohexenyl methyl ketone (10 g) synthesized in Referential Example 1, ethyl alcohol (40 ml) and rhodium trichloride trihydrate (0.9 g). Under stirring, they were reacted at 90° C. for 24 hours. The reaction mixture at this time was sampled and analyzed by gas chromatography, resulting in that the content of trans-2,6,6-trimethyl-3-cyclohexenyl methyl ketone was 11%, while those of 2,6,6-trimethyl-2-cyclohexenyl methyl ketone and 2,6,6-trimethyl-1-cyclohexenyl methyl ketone produced by the above reaction were 87% and 2%, respectively.

Workup

  1. customIn a 200-ml four-necked flask equipped with a thermometer, condenser and a stirrer
  2. customthey were reacted at 90° C. for 24 hours
  3. aliquotThe reaction mixture at this time was sampled

Sources & evidence

ORD record
ord-0e4410c17a534a3fab617a724f481df4
Source dataset
uspto-grants-2004_11
Patent number
US06822121B2

Reaction notes

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