6-(2-Hydroxyethyl)-1,3,3-trimethylbicyclo[2.2.2]octa-5,7-dien-2-one → HCID 21419393, compound

HRID 2397363Notes

Reaction equation

HRID 2397363 reaction equation
[CH3:1][C:2]12[CH:12]=[CH:11][CH:5]([CH:6]=[C:7]1[CH2:8][CH2:9][OH:10])[C:4]([CH3:14])([CH3:13])[C:3]2=[O:15].[H][H]>[Pd].C(O)(C)C>[CH3:1][C:2]12[CH2:12][CH2:11][CH:5]([CH2:6][CH:7]1[CH2:8][CH2:9][OH:10])[C:4]([CH3:14])([CH3:13])[C:3]2=[O:15]

Participants

5

Reactant 2

HCID 213335666-(2-Hydroxyethyl)-1,3,3-trimethylbicyclo[2.2.2]octa-5,7-dien-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 21419393HCID 21419393, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
150 °C

Procedure

An autoclave is charged with 26.8 grams of 1,3,3-trimethyl-6-(2-hydroxyethyl)bicyclo(2.2.2)-octa-5,7-dien-2-one prepared according to the process of Example XVI, 2 grams 5% palladium/carbon catalyst, and 300 ml isopropyl alcohol. The autoclave is then sealed and pressurized with hydrogen to 400 psig, heated to 150° C. and maintained at that temperature, with stirring, for a period of 48 hours. At the end of this period of time, the autoclave is opened and the reaction mass is removed. The reaction mass is filtered, and the excess isopropyl alcohol is stripped therefrom. The reaction product (the title product) is distilled at 64°-65° C. at a pressure of 0.2 mm Hg (yield: 12.3 g). Its structure, confirmed by NMR and mass spectral analyses is as follows: ##STR36##

Workup

  1. customprepared
  2. customThe autoclave is then sealed
  3. temperaturemaintained at that temperature
  4. customthe reaction mass is removed
  5. filtrationThe reaction mass is filtered
  6. distillationThe reaction product (the title product) is distilled at 64°-65° C. at a pressure of 0.2 mm Hg (yield: 12.3 g)

Sources & evidence

ORD record
ord-187fb3a576ec484e8e85562fb24852b7
Source dataset
uspto-grants-1977_05
Patent number
US04021494

Reaction notes

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