Hydrochloric Acid → (2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}prop-2-enoic acid

HRID 523327

Reaktionsgleichung

Reaktionsgleichung von HRID 523327
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[OH-].[K+].[CH3:15][CH2:16][O:17][C:18](Cl)=[O:19].Cl>>[CH2:16]([O:17][C:18]([O:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1)=[O:19])[CH3:15]

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 14797Potassium HydroxideHCID 637542P-Coumaric Acid

Produkt 1

HCID 12876666(2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}prop-2-enoic acidAusbeute 83,6 %

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

67 g (400 mmol) of (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid is added to a mixture of 57.4 g (880 mmol) of potassium hydroxide in 600 ml at 0° C. 46.6 mL (480 mmol) of ethyl chloridocarbonate are added dropwise so that the temperature is maintained to 10° C. The reaction mixture is subsequently allowed to react for 2 hours at 25° C. and then acidified to pH=1 with 200 mL of a 25% HCl solution- The precipitate is filtered off and washed with 500 mL of water. The residue is crystallized in 2 L of toluene and dried under vacuum to yield 79 g (74%) of pure (2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}prop-2-enoic acid as a white powder.

Aufarbeitung

  1. customto react for 2 hours at 25° C.
  2. filtrationis filtered off
  3. washwashed with 500 mL of water
  4. customThe residue is crystallized in 2 L of toluene
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c19f24c05b9d478a89b10cc80c0ebf0b
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334366B2

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