Реакция #2045042

Уравнение реакции

2-(4-nitrophenoxy)propionic acid-2-[2-(4-nitrophenoxy)acetoxy]ethyl ester

2-(4-Nitro-phenoxy)-propionic acid 2-[2-(4-nitro-phenoxy)-acetoxy]-ethyl ester

→

56

Выход 58.0%

2-(4-Aminophenoxy)propionic acid-2-[2-(4-aminophenoxy)acetoxy]ethyl ester

Выход 58.0%

Растворители

dimethylformamide

Условия реакции

Обработка

1. 1
   ДругоеThe catalyst was removed by filtration and ice water (1 L)
2. 2
   workup.ADDITIONwas added to the filtrate
3. 3
   ЭкстракцияCrude 56 was extracted into ethyl acetate
4. 4
   Сушкаdried over Na2SO4
5. 5
   workup.DISTILLATIONdistilled
6. 6
   Другоеpurified by column chromatography on silica gel

Методика

2-(4-nitrophenoxy)propionic acid-2-[2-(4-nitrophenoxy)acetoxy]ethyl ester 55 (20 g, 50 mmol) was dissolved in dry dimethylformamide (150 ml) in a pressure vessel, palladium on carbon (5%, 5 g) added, and the mixture stirred under a hydrogen atm. (4 Kg) for 3 hrs. The catalyst was removed by filtration and ice water (1 L) was added to the filtrate. Crude 56 was extracted into ethyl acetate, dried over Na2SO4, distilled and purified by column chromatography on silica gel using chloroform:ethyl acetate (8:2) to give pure 56 (10 g, 58%) as a dark brown syrup.

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