Epichlorohydrin → 7-(2,3-Epoxypropoxy)flavone

HRID 2291729Notes

Reaction equation

HRID 2291729 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8](=[O:20])[CH:9]=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:11]2)=[CH:6][CH:5]=1.[CH2:21]([CH:23]1[O:25][CH2:24]1)Cl>O>[O:25]1[CH2:24][CH:23]1[CH2:21][O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8](=[O:20])[CH:9]=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 52818947-Hydroxyflavone

Product 1

HCID 99480817-(2,3-Epoxypropoxy)flavone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 82.2 g (2.06 mol) of sodium hydroxide in 585 ml of water were added 3.7 liters of issopropanol and then 490 g (2.06 mol) of 7-hydroxyflavone. To the above mixture were then added 1645 ml (20.5 mol) of epichlorohydrin and the mixture was heated at 70° for 2 hr with stirring. The hot reaction mixture was filtered to remove a solid dimeric by-product. The filtrate was concentrated under reduced pressure (water aspirator) at 50° to 60°. The semisolid residue was treated with 4.4 liters of refluxing isopropanol and more of the dimer from the hot mixture. The clear filtrate on cooling yielded a solid. This was filtered, washed with 600 ml of isopropanol and air dried; yield 434.3 g (72%) of a tan-colored product, m.p. 123°-130° (a pure sample of the title compound melts at 133°-135°.)

Workup

  1. temperaturethe mixture was heated at 70° for 2 hr
  2. filtrationThe hot reaction mixture was filtered
  3. customto remove a solid dimeric by-product
  4. concentrationThe filtrate was concentrated under reduced pressure (water aspirator) at 50° to 60°
  5. additionThe semisolid residue was treated with 4.4 liters of refluxing isopropanol and more of the dimer from the hot mixture
  6. temperatureThe clear filtrate on cooling
  7. customyielded a solid
  8. filtrationThis was filtered
  9. washwashed with 600 ml of isopropanol and air
  10. customdried

Sources & evidence

ORD record
ord-2b1c8e0fd5844e4f9677035e163b1b3c
Source dataset
uspto-grants-1989_01
Patent number
US04797498

Reaction notes

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