Malonic Acid → (2E)-3-(3-Fluorophenyl)-2-propenoic acid

HRID 1449391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1449391
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.C(O)(=O)[CH2:11][C:12]([OH:14])=[O:13].N1C=CC=CC=1.N1CCCCC1>O>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)/[CH:5]=[CH:11]/[C:12]([OH:14])=[O:13]

Komponenten

6

Edukt 4

HCID 867Malonic AcidHCID 1049PyridineHCID 8082PiperidineHCID 680093-Fluorobenzaldehyde

Produkt 1

HCID 1551219(2E)-3-(3-Fluorophenyl)-2-propenoic acidAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 3-fluorobenzaldehyde (40 g), malonic acid (47 g), and an ethanolic solution (150 ml) containing pyridine (10 g) and piperidine (5 g) was heated at reflux with stirring for 8 hours. The reaction mixture was chilled and water (300 ml) was added, giving crystalline trans 3-fluorocinnamic acid which was removed by filtration, washed with water and dried. The trans 3-fluorocinnamic acid, m.p. 162°-163° C., was obtained in 84% yield (44.6 g).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperatureThe reaction mixture was chilled

Quellen und Nachweise

ORD-Eintrag
ord-d9bd647fe788422295575ac60a47a2fa
Quelldatensatz
uspto-grants-1980_02
Patentnummer
US04190674

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