Reacción #2045042

Ecuación de reacción

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

Rendimiento 58.0%

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

Rendimiento 58.0%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente