Réaction #2045037

Équation de réaction

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

Rendement 72.1%

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

Rendement 72.1%

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   AutreThe catalyst was removed by filtration and ice water (3 L)
2. 2
   workup.ADDITIONwas added to the filtrate
3. 3
   ExtractionCrude 50 was extracted into ethyl acetate
4. 4
   Séchagedried over Na2SO4
5. 5
   workup.DISTILLATIONdistilled
6. 6
   Autrepurified by column chromatography on silica gel

Mode opératoire

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.

Source