Potassium Hydroxide → 2-{4-[(4-Chloroanilino)methyl]phenoxy}propanoic acid

HRID 2058090Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2058090
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([NH:6][CH2:7][C:8]2[CH:21]=[CH:20][C:11]([O:12][CH:13]([CH3:19])[C:14]([O:16]CC)=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[K+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:6][CH2:7][C:8]2[CH:21]=[CH:20][C:11]([O:12][CH:13]([CH3:19])[C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:22][CH:23]=1

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 20329856Ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]propionate

Produkt 1

HCID 203298692-{4-[(4-Chloroanilino)methyl]phenoxy}propanoic acidAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In 50 ml of dried methanol are dissolved 10.0 g of ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]propionate and 1.68 g of potassium hydroxide. The mixture is stirred at room temperature for 5 hours. After concentrating the reaction mixture, water is added to the residue, and the resulting solution is washed with ether. The aqueous layer is acidified with hydrochloric acid and extracted with ether. The extract is washed with water, then dried over magnesium sulfate and thereafter the solvent is distilled off. The resulting crystalline residue is recrystallized from benzene to give 8.0 g of 2-[4-(4-chloroanilinomethyl)phenoxy]propionic acid, mp 148° to 149° C.

Aufarbeitung

  1. concentrationAfter concentrating the reaction mixture, water
  2. additionis added to the residue
  3. washthe resulting solution is washed with ether
  4. extractionextracted with ether
  5. washThe extract is washed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationthe solvent is distilled off
  8. customThe resulting crystalline residue is recrystallized from benzene

Quellen und Nachweise

ORD-Eintrag
ord-df8b60be244c4ceea3725cbed2c1dc83
Quelldatensatz
uspto-grants-1980_07
Patentnummer
US04214094

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