Реакция #2045037

Уравнение реакции

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

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

hydrogen

→

50

Выход 72.1%

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

Выход 72.1%

Растворители

dimethylformamide

Условия реакции

Обработка

1. 1
   ДругоеThe catalyst was removed by filtration and ice water (3 L)
2. 2
   workup.ADDITIONwas added to the filtrate
3. 3
   ЭкстракцияCrude 50 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)propionyloxy]ethyl ester 49 (50 g, 89.3 mmol) was dissolved in dry dimethylformamide (400 ml) in a pressure vessel, palladium on carbon (5%, 12.5 g) added, and the mixture stirred under an atm. of hydrogen (4 Kg) for 4 hours. The catalyst was removed by filtration and ice water (3 L) was added to the filtrate. Crude 50 was extracted into ethyl acetate, dried over Na2SO4, distilled and purified by column chromatography on silica gel using chloroform as eluant to give pure 50 (25 g, 58%) as a syrup.

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