Potassium Carbonate → HCID 53907490, 화합물

HRID 26219노트

반응식

HRID 26219 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 53907490HCID 53907490, 화합물수율 135.1%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

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 (1. 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.).

후처리

  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

출처 및 근거

ORD 기록
ord-b38a53ba057347eea338f3c180249e5d
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04148900

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