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

HRID 597340Notes

Reaction equation

HRID 597340 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(O)C.[Pd]>[CH3:1][CH:2]1[CH:11]2[CH:5]([CH:6]([CH3:13])[CH2:7][C:8](=[O:12])[CH2:9][CH2:10]2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

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

Product 1

HCID 214348921,4-Dimethyl-6-oxo-perhydroazulene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

176 mg of 1-methyl-4-methylen-6-oxo-2,3,3a,4,5,6,7,8-octahydroazulene were hydrogenated in 15 ml of ethanol with 175 mg of palladium-on-carbon (5%). After hydrogen uptake was completed the mixture was filtered off from the catalyst, the filtrate evaporated and distilled in vacuum. There was obtained pure 1,4-dimethyl-6-oxo-perhydroazulene; b.p.0.05 60°; IR(film):νmax = 1700, 1460, 1375, 1335, 1250, 1180, 980, 850 cm-1. The compound has a camphorous, herby, woody odour.

Workup

  1. filtrationwas filtered off from the catalyst
  2. customthe filtrate evaporated
  3. distillationdistilled in vacuum

Sources & evidence

ORD record
ord-b460a18f818e4bc3bcfdbfceca56a7f6
Source dataset
uspto-grants-1977_03
Patent number
US04013726

Reaction notes

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