Реакция #725896

Уравнение реакции

(2-bromoethoxy) acetic acid methyl ester

4-nitrophenol

K2CO3

sodium iodide

→

22

Выход 43.6%

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

Выход 43.6%

Растворители

acetone

Условия реакции

Обработка

1. 1
   Температураrefluxed for 24 hours
2. 2
   workup.DISTILLATIONAcetone was distilled off
3. 3
   workup.ADDITIONwater (100 ml) was added
4. 4
   ФильтрацияCrude 22 was filtered
5. 5
   Другоеdried
6. 6
   Другоеpurified by column chromatography on silica gel

Методика

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.

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