Reaction #2045035

Reaction equation

2-(4-Nitro-phenoxy)-propionic acid

ethylene glycol

HCl

→

48

Yield 56.8%

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

Yield 56.8%

Solvents

water

Conditions

Workup

1. 1
   Otherfor 1½ hours
2. 2
   OtherDuring HCl gas bubbling the temp
3. 3
   Otherrose to 60° C
4. 4
   OtherThe crude reaction mass
5. 5
   ExtractionCrude 48 was extracted into chloroform
6. 6
   Dryingdried over Na2SO4
7. 7
   workup.DISTILLATIONdistilled
8. 8
   Otherpurified by column chromatography on silica gel

Procedure

To a mixture of 2-(4-Nitro-phenoxy)-propionic acid 47 (45 g, 213 mol) and ethylene glycol (135 ml) was passed dry HCl gas for 1½ hours. During HCl gas bubbling the temp. rose to 60° C. The crude reaction mass was poured onto cold water (600 ml). Crude 48 was extracted into chloroform, dried over Na2SO4, distilled and purified by column chromatography on silica gel using hexane as eluant to give pure 48 (28 g, 56.8%) as a syrup.

Source