Piperonal → 3',4'-Dimethoxy-3,4-methylenedioxychalcone

HRID 597517

Reaktionsgleichung

Reaktionsgleichung von HRID 597517
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[CH:5]=1)=[O:3].[CH:14]1[C:19]([CH:20]=O)=[CH:18][C:17]2[O:22][CH2:23][O:24][C:16]=2[CH:15]=1.[OH-].[Na+]>C(O)C>[CH3:13][O:12][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[O:10][CH3:11])[C:2](=[O:3])[CH:1]=[CH:20][C:19]1[CH:14]=[CH:15][C:16]2[O:24][CH2:23][O:22][C:17]=2[CH:18]=1

Komponenten

5

Edukt 3

HCID 8438PiperonalHCID 143283,4-Dimethoxyphenyl methyl ketoneHCID 14798Sodium Hydroxide

Produkt 1

HCID 2917283',4'-Dimethoxy-3,4-methylenedioxychalconeAusbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a warm (40° C.) solution of 41.5 grams (0.23 mole) of 3,4-dimethoxyacetophenone and 40.5 grams (0.27 mole) of piperonal in 220 milliliters of ethanol was added 60 milliliters of 10 % aqueous sodium hydroxide. The mixture was warmed for 10 minutes at 40°-50° C; then stirred at room temperature for 2 hours. After standing overnight, the yellow crystalline produce was collected by filtration, washed with water (3 × 40 milliliters), and dried to give 72 grams (quantitative yield) of V, melting point 127°-129° c. An analytical sample was prepared by recrystallization of 1.6 gram of the product from 50 milliliters of ethanol, giving 1.4 gram of pure chalcone as yellow needles, melting point 131°-133° C.; λ (ethanol) 242 (log ε 4.23), 3.60 nm (4.53).

Aufarbeitung

  1. temperatureThe mixture was warmed for 10 minutes at 40°-50° C
  2. waitAfter standing overnight
  3. customthe yellow crystalline produce
  4. filtrationwas collected by filtration
  5. washwashed with water (3 × 40 milliliters)
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-404aec80e95c4e4bb125806d48fa82e6
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04014885

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