Réaction #2045012

Équation de réaction

(2-bromoethoxy) acetic acid methyl ester

4-nitrophenol

K2CO3

sodium iodide

→

22

Rendement 43.6%

[2-(4-Nitrophenoxy)-ethoxy]acetic acid methyl ester

Rendement 43.6%

Solvants

acetone

Conditions de réaction

Traitement

1. 1
   Températurerefluxed for 24 hours
2. 2
   workup.DISTILLATIONAcetone was distilled off
3. 3
   workup.ADDITIONwater (100 ml) was added
4. 4
   FiltrationCrude 22 was filtered
5. 5
   Autredried
6. 6
   Autrepurified by column chromatography on silica gel

Mode opératoire

To a mixture of 4-nitrophenol (5 g, 36 mmol), anhydrous K2CO3 (20 g, 145 mmol) and sodium iodide (2 grams, 13.3 mmol) in anhydrous acetone (100 ml) was added (2-bromoethoxy) acetic acid methyl ester (11 g, 56 mmol) and refluxed for 24 hours. Acetone was distilled off and water (100 ml) was added. Crude 22 was filtered, dried and purified by column chromatography on silica gel using benzene as eluant to give pure 22 (4 g, 43.6%) as a white fluffy powder. The melting point was found to be 96-97.8° C. The structure was confirmed with IR and NMR.

Source