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Hydrochloric Acid → 4'-(Benzyloxy)-5-hydroxy-3,3',7-trimethoxyflavone

HRID 223125
ノート
印刷プレビュー

反応式

HRID 223125 の反応式
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([OH:10])[C:3]=1[C:11](=[O:15])[CH2:12][O:13][CH3:14].[CH2:16]([O:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([O-])=O)=[CH:26][C:25]=1[O:33][CH3:34])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Na+].[OH-].[K+].Cl>C(O)C.C(Cl)(Cl)Cl>[CH2:16]([O:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]2[O:1][C:2]3[C:3]([C:11](=[O:15])[C:12]=2[O:13][CH3:14])=[C:4]([OH:10])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=3)=[CH:26][C:25]=1[O:33][CH3:34])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 205225472',6'-Dihydroxy-2,4'-dimethoxyacetophenoneHCID 23702605Sodium 4-(benzyloxy)-3-methoxybenzoate

生成物 1

HCID 205225384'-(Benzyloxy)-5-hydroxy-3,3',7-trimethoxyflavone収率 62.7%

試薬・触媒・溶媒 2

HCID 702
Ethanol
溶媒
HCID 6212Chloroform溶媒

実験手順

A mixture of 0.67 g of 2',6'-dihydroxy-2,4'-dimethoxyacetophenone, 3.5 g of bis-[4-(benzyloxy)-3-methoxybenzoic] anhydride and 1 g of sodium 4-(benzyloxy)-3-methoxybenzoate was heated at 180°-185° C. under reduced pressure for 3 hours. After cooling, 12 ml of 10% solution of potassium hydroxide in ethanol were added, and the mixture was refluxed under nitrogen for 30 minutes. To the cooled mixture were added 20 ml of 1 N-hydrochloric acid and 100 ml of chloroform, followed by shaking. The organic phase was separated and concentrated under reduced pressure. The residue was chromatographed on silica gel with chloroform. After recrystallization from ethyl acetate/hexane, there was obtained 0.86 g (60% yield) of 4'-(benzyloxy)-5-hydroxy-3,3',7-trimethoxyflavone as yellow crystals: m.p. 156°-157° C.

後処理

  1. temperaturewas heated at 180°-185° C. under reduced pressure for 3 hours
  2. temperatureAfter cooling
  3. temperaturethe mixture was refluxed under nitrogen for 30 minutes
  4. customThe organic phase was separated
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on silica gel with chloroform
  7. customAfter recrystallization from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-cb01904e5f0d4d2db03f6503844c6b67
出典データセット
uspto-grants-1982_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04352792

反応ノート

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