Water → 4-Amino-5-chloro-2-(2-methoxyethoxy)benzoic acid

HRID 2254610

Reaktionsgleichung

Reaktionsgleichung von HRID 2254610
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([NH2:11])=[CH:6][C:5]=1[O:12][CH2:13][CH2:14][O:15][CH3:16].[OH-].[Na+].O>C(O)C>[NH2:11][C:7]1[C:8]([Cl:10])=[CH:9][C:4]([C:3]([OH:17])=[O:2])=[C:5]([O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:6]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 539320764-Amino-5-chloro-2-(2-methoxyethoxy)benzoic acid methyl ester

Produkt 1

HCID 197959774-Amino-5-chloro-2-(2-methoxyethoxy)benzoic acidAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 4-amino-5-chloro-2-(2-methoxyethoxy)benzoic acid methyl ester (2.75 g, 10.6 mmoles) in 95% ethanol (20 ml) was treated with 50% sodium hydroxide (10 ml) and water (10 ml), and refluxed for one hour. The ethanol was removed in vacuo and replaced with water, and the aqueous solution was extracted with ether (20 ml) and adjusted to pH 4 with concentrated hydrochloric acid (16 ml). A resultant precipitate was filtered, washed with water, air dried, and recrystallized from ethyl acetate to yield 2.03 g (78%) of fine pale tan needles, mp 119°-120° C.

Aufarbeitung

  1. temperaturerefluxed for one hour
  2. customThe ethanol was removed in vacuo
  3. extractionthe aqueous solution was extracted with ether (20 ml)
  4. filtrationA resultant precipitate was filtered
  5. washwashed with water, air
  6. customdried
  7. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-02a4994f0c0241dc84fc7c631bbbac03
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05236931

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