Reaction #725912

Reaction equation

(4-nitrophenoxy)acetic acid

(4-Nitro phenoxy) acetic acid

ethylene glycol

HCl

→

41

Yield 57.4%

(4-Nitro-phenoxy)-acetic acid-2-hydroxy-ethyl ester

Yield 57.4%

Conditions

Workup

1. 1
   Otherfor 1 hr
2. 2
   OtherDuring HCl gas bubbling the temperature
3. 3
   Otherrose to 60° C
4. 4
   OtherThe crude reaction mass
5. 5
   workup.ADDITIONwas poured onto ice (2 Kg)
6. 6
   FiltrationCrude 41 was filtered
7. 7
   Otherdried
8. 8
   Otherpurified by column chromatography on silica gel

Procedure

To a mixture of (4-nitrophenoxy)acetic acid 40 (100 g, 507 mmol) and ethylene glycol (300 ml) was passed dry HCl gas for 1 hr. During HCl gas bubbling the temperature rose to 60° C. The crude reaction mass was poured onto ice (2 Kg). Crude 41 was filtered, dried and purified by column chromatography on silica gel using hexane:ethyl acetate (95:5) to give pure 41 (70 g, 57.4%) as a white powder. M.p: 73.5-75.5° C.

Source