6-(Hydroxymethyl)-1,3,3-trimethylbicyclo[2.2.2]octa-5,7-dien-2-one → HCID 21499159, compound

HRID 1730113Notes

Reaction equation

HRID 1730113 reaction equation
[CH3:1][C:2]12[CH:11]=[CH:10][CH:5]([CH:6]=[C:7]1[CH2:8][OH:9])[C:4]([CH3:13])([CH3:12])[C:3]2=[O:14].[H][H]>[C].[Pd].C(O)(C)C>[CH3:1][C:2]12[CH2:11][CH2:10][CH:5]([CH2:6][CH:7]1[CH2:8][OH:9])[C:4]([CH3:13])([CH3:12])[C:3]2=[O:14]

Participants

5

Reactant 2

HCID 214991586-(Hydroxymethyl)-1,3,3-trimethylbicyclo[2.2.2]octa-5,7-dien-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 21499159HCID 21499159, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 30 g of 1,3,3-trimethyl-6-hydroxymethyl-bicyclo-(2.2.2)-octa-5,7-dien-2-one, 0.5 g of 5% of palladium-carbon and 300 ml of isopropyl alcohol is added to a stirred autoclave. The autoclave is pressurized to 400 pounds per square inch with hydrogen and heated to 100° C for 6 hours. At the end of this time, the mixture is filtered, stripped of solvent and vacuum distilled, yielding about 27 g (90%) of the product, 1,3,3-trimethyl-6-hydroxymethyl-bicyclo-(2.2.2)-octan-2-one, having the structure: ##SPC41##

Workup

  1. additionis added to a stirred autoclave
  2. filtrationAt the end of this time, the mixture is filtered
  3. distillationdistilled

Sources & evidence

ORD record
ord-ebf1c271a70a4e36b241c6aa5ef77d1e
Source dataset
uspto-grants-1976_11
Patent number
US03991123

Reaction notes

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