Potassium Permanganate → Furanodienone

HRID 643252Notes

Reaction equation

HRID 643252 reaction equation
[CH3:1][C@@H:2]1[C@:6]23[O:10][C@:9](O)([CH2:11][C:12](=[CH2:13])[C@@H:5]2[CH2:4][CH2:3]1)[C@H:8]([CH:15]([CH3:17])[CH3:16])[CH2:7]3.[Mn]([O-])(=O)(=O)=[O:19].[K+]>C(O)(=O)C>[CH3:16][C:15]1[C:8]2[C:7]([CH:6]=[C:2]([CH3:1])[CH2:3][CH2:4][CH:5]=[C:12]([CH3:13])[CH2:11][C:9]=2[O:10][CH:17]=1)=[O:19]

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 142403924871-97-0

Product 1

HCID 6442374FuranodienoneYield 63%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.45 g (0.01 mol, 96%) of curcumol was dissolved in 40 mL of acetic acid, and to it was added an aqueous solution dissolved with 4 g potassium permanganate. The mixture was heated under reflux for several hours followed by removal of the organic solvent under vacuum. The mixture was extracted with 100 mL of 50% ethyl acetate and water. The ethyl acetate was washed with water several times and dried over anhydrous sodium sulfate. The solvent wad removed under vacuum to afford a dark solid. After separated by silica gel column, 1.45 g of white curzerenone derivative was obtained, yield: 61%, HPLC: 98%, Melting point: 138-140° C., i.e. Compound No. 31 of formula (III) wherein Z is O.

Workup

  1. additionto it was added an aqueous solution
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for several hours
  4. customfollowed by removal of the organic solvent under vacuum
  5. extractionThe mixture was extracted with 100 mL of 50% ethyl acetate and water
  6. washThe ethyl acetate was washed with water several times
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent wad removed under vacuum
  9. customto afford a dark solid
  10. customAfter separated by silica gel column

Sources & evidence

ORD record
ord-641fe30dad61427c99e17e4f9a8d9164
Source dataset
uspto-grants-2010_04
Patent number
US07700584B2

Reaction notes

Loading…