Réaction #170977

Équation de réaction

HCl

(4-nitrophenoxy)acetic acid

(4-Nitrophenoxy)acetic acid

ethylene glycol

→

23

Rendement 57.4%

(4-Nitrophenoxy)-acetic acid-2-hydroxy-ethyl ester

Rendement 57.4%

Conditions de réaction

Traitement

1. 1
   AutreDuring HCl gas bubbling the temperature
2. 2
   Autrerose to 60° C
3. 3
   AutreThe crude reaction mass
4. 4
   workup.ADDITIONwas poured onto ice (2 kg)
5. 5
   FiltrationCrude 23 was filtered
6. 6
   Autredried
7. 7
   Autrepurified by column chromatography on silica gel

Mode opératoire

Dry HCl gas was passed through a mixture of (4-nitrophenoxy)acetic acid 22 (100 g, 507 mmol) and ethylene glycol (300 ml) for 1 hour. During HCl gas bubbling the temperature rose to 60° C. The crude reaction mass was poured onto ice (2 kg). Crude 23 was filtered, dried and purified by column chromatography on silica gel using hexane:ethyl acetate (95:5) to give pure 23 (70 g, 57.4%) as a white powder with an m.p. between 73.5-75.5° C.

Source