Reaction #725896

Reaction equation

(2-bromoethoxy) acetic acid methyl ester

4-nitrophenol

K2CO3

sodium iodide

→

22

Yield 43.6%

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

Yield 43.6%

Solvents

acetone

Conditions

Workup

1. 1
   Temperaturerefluxed 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
   Otherdried
6. 6
   Otherpurified by column chromatography on silica gel

Procedure

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