3-Methyl-8-methylidene-2,4,5,7,8,8a-hexahydroazulen-6(1H)-one → 1,4-Dimethyl-6-oxo-2,3,3a,4,5,6,7,8-octahydroazulene

HRID 597339Notes

Reaction equation

HRID 597339 reaction equation
[CH3:1][C:2]1[CH2:3][CH2:4][CH:5]2[C:11]=1[CH2:10][CH2:9][C:8](=[O:12])[CH2:7][C:6]2=[CH2:13].[H][H]>C(OCC)(=O)C>[CH3:1][C:2]1[CH2:3][CH2:4][CH:5]2[C:11]=1[CH2:10][CH2:9][C:8](=[O:12])[CH2:7][CH:6]2[CH3:13]

Participants

4

Reactant 2

HCID 214348873-Methyl-8-methylidene-2,4,5,7,8,8a-hexahydroazulen-6(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 214349111,4-Dimethyl-6-oxo-2,3,3a,4,5,6,7,8-octahydroazulene

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

528 mg of 1-methyl-4-methylen-6-oxo-2,3,3a,4,5,6,7,8-octahydroazulene were hydrogenated in 20 ml of ethyl acetate with the aid of 200 mg of palladium-on-calcium carbonate (5%). After hydrogen uptake was completed the mixture was filtered off from the catalyst, the filtrate concentrated under reduced pressure and distilled. There was obtained pure 1,4-dimethyl-6-oxo-2,3,3a,4,5,6,7,8-octahydroazulene, b.p.0.06 60°; IR(film):νmax = 1700, 1450, 1378, 1250, 1190 cm-1. The compound has a woody, earthy, camphorous odour.

Workup

  1. filtrationwas filtered off from the catalyst
  2. concentrationthe filtrate concentrated under reduced pressure
  3. distillationdistilled

Sources & evidence

ORD record
ord-a33f128c90fc4c6fa7506be4b101d877
Source dataset
uspto-grants-1977_03
Patent number
US04013726

Reaction notes

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