Acetone → Betulonal

HRID 2180888Notes

Reaction equation

HRID 2180888 reaction equation
[CH3:1][C:2]([C@H:4]1[C@@H:8]2[C@@H:9]3[C@@:22]([CH3:25])([CH2:23][CH2:24][C@@:7]2([CH2:31][OH:32])[CH2:6][CH2:5]1)[C@@:21]1([CH3:26])[C@@H:12]([C@:13]2([CH3:30])[C@@H:18]([CH2:19][CH2:20]1)[C:17]([CH3:28])([CH3:27])[C@@H:16]([OH:29])[CH2:15][CH2:14]2)[CH2:11][CH2:10]3)=[CH2:3].CC(C)=O>O>[CH3:3][C:2]([C@H:4]1[C@@H:8]2[C@@H:9]3[C@@:22]([CH3:25])([CH2:23][CH2:24][C@@:7]2([CH:31]=[O:32])[CH2:6][CH2:5]1)[C@@:21]1([CH3:26])[C@@H:12]([C@:13]2([CH3:30])[C@@H:18]([CH2:19][CH2:20]1)[C:17]([CH3:28])([CH3:27])[C:16](=[O:29])[CH2:15][CH2:14]2)[CH2:11][CH2:10]3)=[CH2:1]

Participants

4

Reactant 2

HCID 180AcetoneHCID 72326Betulin2×

Product 1

HCID 473111Betulonal

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Betulinol was placed in a thermostated reactor, and acetone, in an amount of 100-110 ml per gram of betulinol, was added with stirring. An oxidizing mixture of CrO3/H2SO4 (molar ratio of 2:3, respectively) was then slowly poured into the reactor 20 with stirring. The reaction mixture was brought to reflux and maintained at reflux for 2.5-3 hrs. The reaction mixture was then cooled and water was added, resulting in the formation of a sediment. The sediment was filtered and recrystallized from ethanol. The resulting solid contained 93-95% of betulonic aldehyde and melted at a temperature from 154-156° C. The yield of purified betulonic aldehyde was 65%.

Workup

  1. additionrespectively) was then slowly poured into the reactor 20
  2. stirringwith stirring
  3. temperatureto reflux
  4. temperaturemaintained
  5. temperatureat reflux for 2.5-3 hrs
  6. temperatureThe reaction mixture was then cooled
  7. customresulting in the formation of a sediment
  8. filtrationThe sediment was filtered
  9. customrecrystallized from ethanol
  10. custommelted at a temperature from 154-156° C

Sources & evidence

ORD record
ord-93b0d13b34b040a8abf0bc5d77cbe5ed
Source dataset
uspto-grants-2005_05
Patent number
US06890533B2

Reaction notes

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