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

Participants

Reaction Steps

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°.)

Provenance & Evidence