Water → HCID 13288101, compound

HRID 1981922Notes

Reaction equation

HRID 1981922 reaction equation
[CH:1]([C:4]1[CH:24]=[CH:23][C:7]([C:8]2[O:9][C:10]3[C:15]([C:16](=[O:19])[C:17]=2[CH3:18])=[CH:14][CH:13]=[CH:12][C:11]=3[CH:20]=CC)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[OH2:25].[Mn]([O-])(=O)(=O)=[O:27].[K+].S(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH:1]([C:4]1[CH:24]=[CH:23][C:7]([C:8]2[O:25][C:20]3[C:15]([C:16](=[O:19])[C:17]=2[CH3:18])=[CH:14][CH:13]=[CH:12][C:11]=3[C:10]([OH:9])=[O:27])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 516875Potassium PermanganateHCID 23665763Sodium BisulfiteHCID 53786201HCID 53786201, compound

Product 1

HCID 13288101HCID 13288101, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4'-Isopropyl-3-methyl-8-propenylflavone (3.4 grams) is dissolved in 40 ml of glacial acetic acid, small amount of water is added thereto, 6.6 grams of potassium permanganate is added thereto during eight hours with stirring keeping the inner temperature at 20° to 30° C., then aqueous solution of sodium bisulfite is added thereto keeping the inner temperature at 30° to 40° C., and the mixture is stirred for one hour. Crystals separated out therefrom are collected by filtration, washed with water, dissolved in 10% sodium hydroxide solution, the solution is treated with activated charcoal, filtered, and the filtrate is adjusted to pH 3 with concentrated hydrochloric acid, crystals separated out are collected by filtration, washed with water and recrystallized from methanol to give 1.9 grams of 4'-isopropyl-3-methylflavone-8-carboxylic acid, colorless prisms, melting point 216° to 220° C.

Workup

  1. customat 20° to 30° C.
  2. customat 30° to 40° C.
  3. stirringthe mixture is stirred for one hour
  4. customCrystals separated
  5. filtrationout therefrom are collected by filtration
  6. washwashed with water
  7. dissolutiondissolved in 10% sodium hydroxide solution
  8. additionthe solution is treated with activated charcoal
  9. filtrationfiltered
  10. customseparated out
  11. filtrationare collected by filtration
  12. washwashed with water
  13. customrecrystallized from methanol

Sources & evidence

ORD record
ord-8f9c7cc3448f49a29ba325e1009b09ed
Source dataset
uspto-grants-1986_06
Patent number
US04594345

Reaction notes

Loading…