4-Ethoxybenzaldehyde → 3-(4-Ethoxycinnamoyl)-7-methoxycoumarin

HRID 25874

Reaktionsgleichung

Reaktionsgleichung von HRID 25874
[C:1]([C:4]1[C:5](=[O:16])[O:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([O:14][CH3:15])[CH:8]=2)(=[O:3])[CH3:2].[CH2:17]([O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1)[CH3:18]>N1CCCCC1.C(#N)C>[CH2:17]([O:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[CH:2][C:1]([C:4]2[C:5](=[O:16])[O:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[C:9]([O:14][CH3:15])[CH:8]=3)=[O:3])=[CH:22][CH:21]=1)[CH3:18]

Komponenten

5

Edukt 2

HCID 248344-EthoxybenzaldehydeHCID 20544753-Acetyl-7-methoxycoumarin

Produkt 1

HCID 541146183-(4-Ethoxycinnamoyl)-7-methoxycoumarin

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8082PiperidineKatalysator2×HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A suspension of 2.18 g 3-acetyl-7-methoxycoumarin and 1.65 g p-ethoxybenzaldehyde in 100 ml alcohol was heated under reflux on a steam bath. Acetonitrile was added until solution was attained. Fifty drops of piperidine were added and the reaction mixture heated under reflux for 90 minutes. An additional fifty drops of piperidine were added and the solution was heated under reflux another hour. The product separated upon cooling and was washed with alcohol before being recrystallized from a mixture of alcohol and acetonitrile.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux on a steam bath
  3. temperaturethe reaction mixture heated
  4. temperatureunder reflux for 90 minutes
  5. temperaturethe solution was heated
  6. temperatureunder reflux another hour
  7. customThe product separated
  8. temperatureupon cooling
  9. washwas washed with alcohol
  10. custombefore being recrystallized from a mixture of alcohol and acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-943fff4c598841fc8e0531cb49187a38
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04147552

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