Reaction #2045042

Reaction equation

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

Yield 58.0%

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

Yield 58.0%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   OtherThe 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
   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)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