Reaction #2045037

Reaction equation

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

Yield 72.1%

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

Yield 72.1%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   OtherThe 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
   Dryingdried over Na2SO4
5. 5
   workup.DISTILLATIONdistilled
6. 6
   Otherpurified by column chromatography on silica gel

Procedure

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