Pyridine → 4-Methoxycinnamic acid chloride

HRID 707735

Reaktionsgleichung

Reaktionsgleichung von HRID 707735
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9](O)=[O:10])=[CH:5][CH:4]=1.N1C=CC=CC=1.O=S(Cl)[Cl:22]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([Cl:22])=[O:10])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 132454-Methoxy cinnamic acidHCID 24386Thionyl Chloride

Produkt 1

HCID 534017724-Methoxycinnamic acid chlorideAusbeute 94,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A first 3 L, 4 necked round bottomed flask (RBF) was equipped with a mechanical stirrer, thermowell, and a condenser with nitrogen adapter. The RBF was charged with 4-methoxycinnamic acid (175 g, 982 mmol) and 0.1 mL dry pyridine in 2 L dry toluene. The addition funnel was charged with 107.2 mL (1.473 mol) SOCl2 which was then added slowly to the reaction mixture at room temperature. The reaction mixture was heated to reflux and monitored by GC analysis (aliquots were withdrawn periodically, quenched with MeOH, and analyzed). After 5 hours, the GC analysis indicated that the reaction was complete and the reaction mixture was allowed to cool to room temperature. Excess SOCl2 and toluene were removed by rotary evaporation and the crude product was purified by distillation to give 182 g of 4-methoxycinnamoyl chloride (94% yield) with 98.9% purity by GC.

Aufarbeitung

  1. customA first 3 L, 4 necked round bottomed flask (RBF) was equipped with a mechanical stirrer
  2. additionwas then added slowly to the reaction mixture at room temperature
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux
  5. customwere withdrawn periodically
  6. customquenched with MeOH
  7. customExcess SOCl2 and toluene were removed by rotary evaporation
  8. distillationthe crude product was purified by distillation

Quellen und Nachweise

ORD-Eintrag
ord-1c3347ca8f964996a97f97d05fd92ac0
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09175123B2

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