5H-Inden-5-one, 7-butyl-1,2,3,6,7,7a-hexahydro- → 5H-Inden-5-one, 7-butyloctahydro-

HRID 1659666Notes

Reaction equation

HRID 1659666 reaction equation
[CH2:1]([CH:5]1[CH:13]2[C:9]([CH2:10][CH2:11][CH2:12]2)=[CH:8][C:7](=[O:14])[CH2:6]1)[CH2:2][CH2:3][CH3:4]>C(OCC)(=O)C.[Pd]>[CH2:1]([CH:5]1[CH:13]2[CH:9]([CH2:10][CH2:11][CH2:12]2)[CH2:8][C:7](=[O:14])[CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 205598595H-Inden-5-one, 7-butyl-1,2,3,6,7,7a-hexahydro-

Product 1

HCID 211560605H-Inden-5-one, 7-butyloctahydro-Yield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-Butylbicyclo [4.3.0] non-1-en-3-one (120 g) is hydrogenated in ethyl acetate (125 ml) over 1.5 g of 5% palladium on carbon at a pressure of 4 atmospheres in a Parr apparatus. The solution is filtered through celite to remove the catalyst, concentrated, and the residue is vacuum distilled through a 12" Vigreaux column to yield 114 g (bp 98°-102° C. at 0.5 mm) of 5-butylbicyclo [4.3.0] nonan-3-one represented by the structure: ##STR10##

Workup

  1. filtrationThe solution is filtered through celite
  2. customto remove the catalyst
  3. concentrationconcentrated
  4. distillationdistilled through a 12" Vigreaux column

Sources & evidence

ORD record
ord-adfa4b7450294f9885a10b203db1fdd3
Source dataset
uspto-grants-1981_12
Patent number
US04304944

Reaction notes

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