Ethylbenzene → Cyclohexanone, 2-(2-methyl-2-propenyl)-

HRID 1902189Notes

Reaction equation

HRID 1902189 reaction equation
C(=O)(O[CH2:6][C:7](=[CH2:9])[CH3:8])OCC.[C:11]1(=[O:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(C1C=CC=CC=1)C>[Pd].O1CCCC1>[CH2:8]([CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C:11]1=[O:17])[C:7](=[CH2:6])[CH3:9]

Participants

7

Reactant 4

HCID 7500EthylbenzeneHCID 7967Cyclohexanone2×HCID 11776TriphenylphosphineHCID 11094742ethyl methallyl carbonate

Product 1

HCID 11829651Cyclohexanone, 2-(2-methyl-2-propenyl)-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture containing ethyl methallyl carbonate (1.44 g, 0.010 mole), cyclohexanone (0.98 g, 0.010 mole), 5 percent palladium on carbon (1.0 g), triphenylphosphine (0.20 g, 0.76 mmole), and tetrahyrofuran (15 ml) was refluxed under N2 for 22 hours. Gas chromatographic quantification by means of an internal standard (ethylbenzene) showed 41.6 percent of the cyclohexanone has been consumed and that the desired product, 2-methallylcyclohexanone was formed in 49.2 yield based on unrecovered cyclohexanone. Preparative gas chromatography of the crude mixture gave a pure sample of the product whose structure was confirmed by infrared and nuclear magnetic resonance spectroscopy.

Workup

  1. temperaturewas refluxed under N2 for 22 hours
  2. customhas been consumed and that the desired product

Sources & evidence

ORD record
ord-9bacf8af02d0472988be2abdf86b1363
Source dataset
uspto-grants-1982_12
Patent number
US04362670

Reaction notes

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