Réaction #725923

Équation de réaction

6-(4-nitrophenoxy)hexanoic acid

6-(4-Nitrophenoxy)-hexanoic acid

ethylene glycol

HCl

→

54

Rendement 78.3%

6-(4-Nitrophenoxy)hexanoic acid 2-hydroxyethyl ester

Rendement 78.3%

Conditions de réaction

Traitement

1. 1
   Autrefor one hr
2. 2
   AutreDuring HCl gas bubbling the temp
3. 3
   Autrerose to 60° C
4. 4
   AutreThe crude reaction mass
5. 5
   workup.ADDITIONwas poured onto ice (1 Kg)
6. 6
   Extractionextracted into ethyl acetate
7. 7
   Lavagewashed with water (2×250 ml)
8. 8
   Séchagedried over sodium sulphate
9. 9
   workup.DISTILLATIONdistilled
10. 10
    Autreto get crude 54, which
11. 11
    Autrewas purified by column chromatography on silica gel

Mode opératoire

To a mixture of 6-(4-nitrophenoxy)hexanoic acid 53 (50 g, 197.62 mmol) and ethylene glycol(200 ml) was passed dry HCl gas for one hr. During HCl gas bubbling the temp. rose to 60° C. The crude reaction mass was poured onto ice (1 Kg), extracted into ethyl acetate, washed with water (2×250 ml), dried over sodium sulphate and distilled to get crude 54, which was purified by column chromatography on silica gel using benzene as eluant to get pure 54 (46 g, 78.3%) as a light yellow syrup.

Source