6-Hydroxy-1,4-dimethyl-2,3,3a,4,5,6,7,8-octahydroazulene → 6-Hydroxy-1,4-dimethyl-perhydroazulene

HRID 597315Notes

Reaction equation

HRID 597315 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])[CH:4]([CH3:13])[CH2:3]1>C(O)C.[Pd]>[OH:1][CH:2]1[CH2:11][CH2:10][CH:9]2[CH:5]([CH2:6][CH2:7][CH:8]2[CH3:12])[CH:4]([CH3:13])[CH2:3]1

Participants

4

Reactant 1

HCID 214349076-Hydroxy-1,4-dimethyl-2,3,3a,4,5,6,7,8-octahydroazulene

Product 1

HCID 214474806-Hydroxy-1,4-dimethyl-perhydroazuleneYield 68.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3.6 g of 6-hydroxy-1,4-dimethyl-2,3,3a, 4,5,6,7,8-octahydroazulene were hydrogenated in 25 ml of ethanol with 500 mg of palladium-on-carbon (10%). The reaction mixture was filtered, the filtrate evaporated and distilled under reduced pressure in a bulb-tube. There were obtained 2.5 g of 6-hydroxy-1,4-dimethyl-perhydroazulene; b.p.0.005 ca 82°; IR(film):νmax = 3360, 1460, 1375, 1030, 975 cm-1. The compound has a fresh, woody, earthy odour somewhat reminiscent of vetiver.

Workup

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

Sources & evidence

ORD record
ord-5e27d01da16a4aefa8e7e553495ba4cc
Source dataset
uspto-grants-1977_03
Patent number
US04013711

Reaction notes

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