6-(Carbethoxymethyl)-3-phenyl-2-cyclohexen-1-one → HCID 19898346, compound

HRID 1196423Notes

Reaction equation

HRID 1196423 reaction equation
[C:1]([CH2:6][CH:7]1[C:12](=[O:13])[CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)([O:3][CH2:4][CH3:5])=[O:2]>[Pd].C(OCC)(=O)C>[C:1]([CH2:6][CH:7]1[C:12](=[O:13])[CH2:11][CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 1

HCID 216716106-(Carbethoxymethyl)-3-phenyl-2-cyclohexen-1-one

Product 1

HCID 19898346HCID 19898346, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

6-(Carbethoxymethyl)-3-phenyl-2-cyclohexen-1-one (2.11 g) was added to a mixture of 0.2 g of 10% palladium on carbon in 30 ml of ethyl acetate. The reaction mixture was hydrogenated under a hydrogen atmosphere (maximum pressure 45 psi) for 41 hours. The mixture was filtered through celite, and the solvent was removed under reduced pressure. The recovered crude oil product was purified by chromatography on silica gel eluted with 5% ethyl acetate in hexane to provide 1.5 g (71%) of 6-(carbethoxymethyl)-3-phenylcyclohexanone.

Workup

  1. customfor 41 hours
  2. filtrationThe mixture was filtered through celite
  3. customthe solvent was removed under reduced pressure
  4. customThe recovered crude oil product
  5. customwas purified by chromatography on silica gel
  6. washeluted with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-7c46a809bee84b7e9caf67792ad49c77
Source dataset
uspto-grants-1992_05
Patent number
US05114493

Reaction notes

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