Reaktion #5468

Reaktionsgleichung

4-amino-5-chloro-2-(2-methoxyethoxy)benzoic acid methyl ester

sodium hydroxide

water

→

fine pale tan needles

Ausbeute 78.0%

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

Ausbeute 78.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed for one hour
2. 2
   SonstigeThe ethanol was removed in vacuo
3. 3
   ExtraktionThe aqueous solution was extracted with ether (20 mL)
4. 4
   SonstigeA solid soon precipitated
5. 5
   Filtrationthis was filtered
6. 6
   Waschenwashed with water, air
7. 7
   Sonstigedried
8. 8
   Sonstigerecrystallized from ethyl acetate (2 crops)

Vorschrift

A solution of 4-amino-5-chloro-2-(2-methoxyethoxy)benzoic acid methyl ester (2.75 g, 10.6 mmol) 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. The aqueous solution was extracted with ether (20 mL) and acidified to pH 4 with concentrated hydrochloric acid (16 mL). A solid soon precipitated, and this was filtered, washed with water, air dried, and recrystallized from ethyl acetate (2 crops) to afford 2.03 g (75%) of fine pale tan needles; mp 119°-120° C.

Quelle