Reaction #170985

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

→

32

Yield 72.1%

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

Yield 72.1%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   OtherCatalyst was removed by filtration and ice water (3 L)
2. 2
   workup.ADDITIONwas added to the filtrate
3. 3
   ExtractionCrude 32 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 31 (50 g, 89.3 mmol) was dissolved in dry dimethylformamide (400 ml) in a pressure vessel. Palladium on carbon (5%, 12.5 g) was added, and the mixture stirred under an atmosphere of hydrogen (4 kg) for 4 hours. Catalyst was removed by filtration and ice water (3 L) was added to the filtrate. Crude 32 was extracted into ethyl acetate, dried over Na2SO4, and distilled and purified by column chromatography on silica gel using chloroform as eluant to give pure 32 (25 g, 58%) as a syrup.

Source