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

HRID 478080ノート

反応式

HRID 478080 の反応式
[OH-].[Na+].[CH:3]([OH:6])([CH3:5])[CH3:4].[OH:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12](=[O:24])[CH:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:15]2)=[CH:10][CH:9]=1.C(C1OC1)Cl>O>[O:6]1[CH2:5][CH:3]1[CH2:4][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12](=[O:24])[CH:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:15]2)=[CH:10][CH:9]=1

参加物

6

反応物 4

HCID 3776IsopropanolHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 52818947-Hydroxyflavone

生成物 1

HCID 99480817-(2,3-Epoxypropoxy)flavone

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

To a solution of 82.2 g (2.06 mol) of sodium hydroxide in 585 ml of water were added 3.7 liters of isopropanol and then 490 g (2.06 mole) of 7-hydroxyflavone. To the above mixture were then added 1645 ml (20.5 mole) of epichlorohydrin and the mixture heated at 70° C. for 2 hours with stirring. The hot reaction mixture was filtered to remove dimeric by-product. The filtrate was concentrated under reduced pressure (water aspirator) at 50°-60° C. The semisolid residue was treated with 4.4 liters of refluxing isopropanol and more of the dimer filtered 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, mp 123°-130° C. (a pure sample melts at 133°-135° C. from i-PrOH). The crude epoxide was used for further reaction.

後処理

  1. filtrationThe hot reaction mixture was filtered
  2. customto remove dimeric by-product
  3. concentrationThe filtrate was concentrated under reduced pressure (water aspirator) at 50°-60° C
  4. additionThe semisolid residue was treated with 4.4 liters of refluxing isopropanol and more of the dimer
  5. filtrationfiltered 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
  11. customThe crude epoxide was used for further reaction

出典と根拠

ORDレコード
ord-e711f5b358f5408880e3b2f46cab5036
出典データセット
uspto-grants-1989_12
特許番号
US04889941

反応ノート

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