Ethanol → Benzoic acid, 4-chloro-2-hydroxy-, ethyl ester

HRID 228605

Reaktionsgleichung

Reaktionsgleichung von HRID 228605
[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].Cl.CN(C)[CH2:15][CH2:16]CN=C=N.O.ON1C2C=CC=CC=2N=N1.C(O)C>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([O:8][CH2:15][CH3:16])=[O:7]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 787824-Chlorosalicylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 21899179Dimethylaminopropyl carbodiimide hydrochloride

Produkt 1

HCID 12548597Benzoic acid, 4-chloro-2-hydroxy-, ethyl esterAusbeute 43,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Chlorosalicylic acid (344 mg), 1-ethyl-3-(3-dimethylaminopropylcarbodiimide hydrochloride (420 mg), 1-hydroxybenzotriazole hydrate (337 mg), and ethanol (2 ml) were dissolved in N,N-dimethylformamide to prepare a solution which was then stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give ethyl 4-chlorosalicylate (174 mg, yield 43%).

Aufarbeitung

  1. customto prepare a solution which
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. distillationby distillation under the reduced pressure
  7. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-63f94f5e381e42159b80935652026ca1
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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