Réaction #2045042

Équation de réaction

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

Rendement 58.0%

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

Rendement 58.0%

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   AutreThe catalyst was removed by filtration and ice water (1 L)
2. 2
   workup.ADDITIONwas added to the filtrate
3. 3
   ExtractionCrude 56 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)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.

Source