Reacción #2045037

Ecuación de reacción

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

Rendimiento 72.1%

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

Rendimiento 72.1%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe catalyst was removed by filtration and ice water (3 L)
2. 2
   workup.ADDITIONwas added to the filtrate
3. 3
   ExtracciónCrude 50 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)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.

Fuente