Hydrochloric Acid → 4-Chloro-3-fluorocinnamic acid

HRID 1774155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1774155
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[F:10].C(O)(=O)[CH2:12][C:13]([OH:15])=[O:14].N1C=CC=CC=1.Cl>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:12]/[C:13]([OH:15])=[O:14])=[CH:4][C:3]=1[F:10]

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 1049PyridineHCID 27249854-Chloro-3-Fluorobenzaldehyde

Produkt 1

HCID 57084034-Chloro-3-fluorocinnamic acidAusbeute 92,7 %

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

4-Chloro-3-fluorobenzaldehyde (15.0 g, 94.6 mmol) was combined with malonic acid (10.8 g, 104 mmol) and pyridine (11.5 mL, 142 mmol). The mixture was heated to 50° C. and agitated 1 hour. Then it was heated to 100° C. and agitated 16 hours. Ice (100 g) and 6M HCl (25 mL) were added, and the mixture was agitated one hour. Precipitation was filtered, washed with water and dried in vacuo to give (E)-3-(4-chloro-3-fluorophenyl)acrylic acid (17.6 g, 87.7 mmol, 92.7% yield) as a solid.

Aufarbeitung

  1. temperatureThen it was heated to 100° C.
  2. stirringagitated 16 hours
  3. stirringthe mixture was agitated one hour
  4. customPrecipitation
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f27530d6ad404f58b3bf8350da17f6aa
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09259470B2

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