HCID 21333567, compound → HCID 21333572, compound

HRID 1390646Notes

Reaction equation

HRID 1390646 reaction equation
[CH3:1][C:2]1([CH3:14])[CH:7]2[CH:8]=[CH:9][CH:4]([C:5]([CH2:10][CH2:11][OH:12])=[CH:6]2)[C:3]1=[O:13].[H][H]>[Pd].C(O)(C)C>[CH3:1][C:2]1([CH3:14])[CH:7]2[CH2:8][CH2:9][CH:4]([CH:5]([CH2:10][CH2:11][OH:12])[CH2:6]2)[C:3]1=[O:13]

Participants

5

Reactant 2

HCID 21333567HCID 21333567, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21333572HCID 21333572, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 60 g of 3,3-dimethyl-6-(2-hydroxyethyl)-bicyclo(2.2.2)-octa-5,7-diene-2-one produced according to Example I, 300 ml of isopropyl alcohol and 5 g of 5% palladium on charcoal catalyst is placed in an autoclave. The autoclave is pressurized with hydrogen and heated to 100° C. for six hours. The resulting reaction mixture is filtered and the solvent is removed by vacuum stripping. Distillation of the residue through a 3" microvigreaux column yields 55 g of 3,3-dimethyl-6-(2-hydroxyethyl)-bicyclo(2.2.2)-octanone having the structure: ##STR27##

Workup

  1. customproduced
  2. customThe resulting reaction mixture
  3. filtrationis filtered
  4. customthe solvent is removed by vacuum stripping
  5. distillationDistillation of the residue through a 3" microvigreaux column

Sources & evidence

ORD record
ord-b678bb4d24b340ba93ff9f89de25584b
Source dataset
uspto-grants-1979_02
Patent number
US04139650

Reaction notes

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