Oxalyl chloride → Cinnamoyl Chloride

HRID 53350

Reaktionsgleichung

Reaktionsgleichung von HRID 53350
[C:1]([OH:11])(=O)/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(Cl)(=O)C([Cl:15])=O>C1(C)C=CC=CC=1>[C:1]([Cl:15])(=[O:11])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

4

Edukt 2

HCID 65578Oxalyl chlorideHCID 444539Cinnamic Acid

Produkt 1

HCID 5354261Cinnamoyl ChlorideAusbeute 135,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

trans-Cinnamic acid (5 g, 33.7 mmol, Aldrich) was dissolved in toluene (100 mL), and the solution was cooled to 0° C. and flushed with N2. Anhydrous DMF (0.1 mL) was added, followed by oxalyl chloride (8.56 g, 5.88 mL, 67.4 mmol) dropwise over 8 minutes. The mixture was stirred at 0° C. for 1 hour and at room temperature for 1.5 hours. The solvent was removed under vacuum to give the title compound (7.63 g).

Aufarbeitung

  1. customflushed with N2
  2. additionAnhydrous DMF (0.1 mL) was added
  3. customThe solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5922897b2fd84ef282b4a00b663a2f4c
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05618949

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