3-Methyl-8-methylidene-1,2,4,5,6,7,8,8a-octahydroazulen-6-ol → 6-Hydroxy-1,4-dimethyl-2,3,3a,4,5,6,7,8-octahydroazulene

HRID 597314Notes

Reaction equation

HRID 597314 reaction equation
[OH:1][CH:2]1[CH2:11][CH2:10][C:9]2[CH:5]([CH2:6][CH2:7][C:8]=2[CH3:12])[C:4](=[CH2:13])[CH2:3]1.[H][H]>C(O)C.[Pt]=O>[OH:1][CH:2]1[CH2:11][CH2:10][C:9]2[CH:5]([CH2:6][CH2:7][C:8]=2[CH3:12])[CH:4]([CH3:13])[CH2:3]1

Participants

5

Reactant 2

HCID 214348863-Methyl-8-methylidene-1,2,4,5,6,7,8,8a-octahydroazulen-6-olHCID 178418361HCID 178418361, compound

Product 1

HCID 214349076-Hydroxy-1,4-dimethyl-2,3,3a,4,5,6,7,8-octahydroazuleneYield 60.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

500 mg of platinum oxide were pre-hydrogenated in 300 ml of ethanol. After addition of 2.14 g of 6-hydroxy-1-methyl-4-methylen-2,3,3a, 4,5,6,7,8-octahydroazulene, the mixture was hydrogenated until hydrogen was no longer taken up. The reaction mixture was filtered, the filtrate evaporated and the crude product distilled under reduced pressure in a bulb-tube. There were obtained 1.3 g of pure 6-hydroxy-1,4-dimethyl-2,3,3a, 4,5,6,7,8-octahydroazulene; b.p.0.001 ca 85°; IR(film):νmax 3380, 1460, 1440, 1095, 1078, 1035/30, 985/75, 940 cm-1. The substance has a woody, flowery, fresh green odour.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated
  3. distillationthe crude product distilled under reduced pressure in a bulb-tube

Sources & evidence

ORD record
ord-dece4b05fa834736bd181ddbd88e5518
Source dataset
uspto-grants-1977_03
Patent number
US04013711

Reaction notes

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