HCID 86739281, compound → 1,3,3,5,6-Pentamethylbicyclo[2.2.2]oct-5-en-2-one

HRID 2413380Notes

Reaction equation

HRID 2413380 reaction equation
C(O)(=O)C.C(O)(=O)C.O[CH2:10][C:11]1[CH:12]2[CH:20]=[CH:19][C:15]([CH3:21])([C:16]=1[CH2:17]O)[C:14](=[O:22])[C:13]2([CH3:24])[CH3:23]>[Pd].C(O)(C)C>[CH3:21][C:15]12[CH2:19][CH2:20][CH:12]([C:11]([CH3:10])=[C:16]1[CH3:17])[C:13]([CH3:24])([CH3:23])[C:14]2=[O:22]

Participants

4

Reactant 1

HCID 86739281HCID 86739281, compound

Product 1

HCID 202613161,3,3,5,6-Pentamethylbicyclo[2.2.2]oct-5-en-2-oneYield 119.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a 450 ml Parr mini-pressure reactor is charged 15 grams of 5,6-bis(hydroxymethyl)-1,3,3-trimethylbicyclo[2.2.2]-octa-5,7-dien-2-one diacetate produced according to Example IV, 60 ml of isopropyl alcohol and 0.3 grams of 10% palladium on charcoal. After flushing with nitrogen and hydrogen, the hydrogen is charged to a pressure of 195 psig while maintaining the reaction mass temperature at 22°-27° C. Within four minutes, the pressure drops to 140 psig and holds steady for six minutes. Hydrogen is again charged to 195 psig and the temperature is gradually raised to 80° C. At 80° C. the pressure begins to drop. The temperature is raised to 85° C. and maintained at 85° C. until the pressure holds constant at 102 psig (1.7 hours). After cooling to room temperature, the reaction mass is filtered and the toluene is removed in vacuo to yield 10.1 grams of 1,3,3,5,6-pentamethyl-bicyclo[2.2.2]octa-5-en-2-one. This material is identical to that prepared from 2,6,6-trimethylcyclohexa-2,4-dien-1-one and 2-butyne according to Examples I and II, supra.

Workup

  1. customproduced
  2. customAfter flushing with nitrogen and hydrogen
  3. additionthe hydrogen is charged to a pressure of 195 psig
  4. temperaturewhile maintaining the reaction mass temperature at 22°-27° C
  5. waitholds steady for six minutes
  6. additionHydrogen is again charged to 195 psig
  7. customAt 80° C.
  8. temperatureThe temperature is raised to 85° C.
  9. temperaturemaintained at 85° C. until the pressure
  10. customholds constant at 102 psig (1.7 hours)
  11. temperatureAfter cooling to room temperature
  12. filtrationthe reaction mass is filtered
  13. customthe toluene is removed in vacuo

Sources & evidence

ORD record
ord-5ac5ebdcda2c43b98f5d9566cf2d1234
Source dataset
uspto-grants-1985_01
Patent number
US04496775

Reaction notes

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