Potassium Carbonate → HCID 53907490、化合物

HRID 462118ノート

反応式

HRID 462118 の反応式
[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[O:14]C(=O)C=CC1C=CC=CC=1)[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2].[C:25](=[O:28])([O-])[O-].[K+].[K+]>CC(CC)=O>[OH:14][C:13]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[C:1]([CH2:2][C:25](=[O:28])[CH:2]=[CH:1][C:4]1[CH:5]=[CH:6][CH:11]=[CH:12][CH:13]=1)=[O:3]

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 53983899Methyl 3-acetyl-4-cinnamoyloxy-benzoate

生成物 1

HCID 53907490HCID 53907490、化合物収率 135.1%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

Methyl 3-acetyl-4-cinnamoyloxy-benzoate (46.2 g; m.p. 97°-99° C) was dissolved in methyl-ethyl-ketone (350 ml). After addition of anhydrous potassium carbonate (37 g), the mixture was refluxed for 6 hours. After cooling, dilution with petroleum ether (500 ml) and filtration, the collected precipitate was dissolved in water, acidified with acetic acid, extracted with ethylacetate. The organic phase was washed with potassium carbonate 5% and water, then evaporated to dryness. After crystallisation from methanol, (2-hydroxy-5-carbomethoxy-benzoyl)-cinnamoyl-methane (31.2 g; m.p. 138°-140° C) was obtained, which was refluxed for 15 minutes with formic acid 99% (140 ml). After cooling, dilution with water (l. 1) and filtration, the collected precipitate was crystallised from acetone to obtain 6-carbomethoxy-2-(β-phenylvinyl)-chromone (27.8 g; m.p. 175°-177° C) which was hydrolysed with a solution of potassium hydroxide 1% (600 ml) in ethanol 95% at reflux temperature for 45 minutes. After cooling, acidification with acetic acid, concentration under vacuum and dilution with water, the precipitate was collected and washed with water to give, after crystallisation from acetone, 6-carboxy-2-(β-phenyl-vinyl)-chromone (16.1 g; m.p. 273°-275° C).

後処理

  1. temperaturethe mixture was refluxed for 6 hours
  2. temperatureAfter cooling
  3. filtrationdilution with petroleum ether (500 ml) and filtration
  4. dissolutionthe collected precipitate was dissolved in water
  5. extractionextracted with ethylacetate
  6. washThe organic phase was washed with potassium carbonate 5% and water
  7. customevaporated to dryness
  8. customAfter crystallisation from methanol

出典と根拠

ORDレコード
ord-f4c3ccebf6b54319b19b1d2f9677f9a6
出典データセット
uspto-grants-1977_12
特許番号
US04065467

反応ノート

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