HCID 178442260, compound → Hulupone

HRID 597327Notes

Reaction equation

HRID 597327 reaction equation
[CH3:1][CH:2]([CH2:4][C:5]([C:7]1[C:13]([OH:14])=C(CC=C(C)C)[C:10](=[O:11])[C:9]([CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])([CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])[C:8]=1[OH:30])=[O:6])[CH3:3]>[OH-].[Na+]>[CH3:1][CH:2]([CH2:4][C:5]([CH:7]1[C:8](=[O:30])[C:9]([CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])([CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])[C:10](=[O:11])[C:13]1=[O:14])=[O:6])[CH3:3]

Participants

3

Reactant 1

HCID 178442260HCID 178442260, compound

Product 1

HCID 549598Hulupone

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

4 g lupulone are dissolved, with stirring, in 100 ml 0.5 N sodium hydroxide solution, filtered into a 250 ml three necked flask provided with a gas inlet tube, reflux condenser, and internal thermometer, and mixed with 1 g catalyst (see Table). After flushing out with oxygen, the apparatus is heated to the predetermined temperature. The lupulate solution is then oxidized with vigorous stirring, while oxygen is passed through. After completion of the reaction, which can be recognized by a marked fall in the absorption of oxygen, or after the consumption of 250 ml of oxygen, the solution is allowed to cool, the catalyst is filtered off, and the solution is acidified and twice extracted with 50 ml n-hexane on each occasion. The combined hexane solutions are dried over sodium sulphate and evaporated. The hulupone is obtained in the form of a bright yellow to brownish yellow oil (see Table).

Workup

  1. filtrationfiltered into a 250 ml three necked flask
  2. customprovided with a gas inlet tube
  3. temperaturereflux condenser
  4. customAfter flushing out with oxygen
  5. temperaturethe apparatus is heated to the predetermined temperature
  6. customAfter completion of the reaction, which
  7. customcan be recognized by a marked fall in the absorption of oxygen
  8. customafter the consumption of 250 ml of oxygen
  9. temperatureto cool
  10. filtrationthe catalyst is filtered off
  11. extractiontwice extracted with 50 ml n-hexane on each occasion
  12. dry with materialThe combined hexane solutions are dried over sodium sulphate
  13. customevaporated

Sources & evidence

ORD record
ord-9080c23144b14075a476803657b158c7
Source dataset
uspto-grants-1977_03
Patent number
US04013721

Reaction notes

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