Reaction #2045036

Reaction equation

1,3-dicyclohexyl carbodiimide

2-(4-nitrophenoxy) propionic acid

2-(4-Nitro-phenoxy)-propionic acid

2-(4-nitrophenoxy)propionic acid 2-hydroxyethyl ester

2-(4-Nitro-phenoxy)-propionic acid 2-hydroxy-ethyl ester

→

49

Yield 35.1%

2-(4-Nitrophenoxy)propionic acid 2-[2-(4-nitrophenoxy)propionyloxy]ethyl ester

Yield 35.1%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   FiltrationThe solids were filtered off
2. 2
   workup.DISTILLATIONdichloromethane distilled off
3. 3
   Otherto get crude 49
4. 4
   OtherThe crude 49 was purified by column chromatography on silica gel

Procedure

To a mixture of 2-(4-nitrophenoxy) propionic acid 47 (25 grams, 118.5 mmol) and 2-(4-nitrophenoxy)propionic acid 2-hydroxyethyl ester 48 (25 grams, 108 mmol) in anhydrous dichloromethane (625 ml) under nitrogen atm. was added dropwise a solution of 1,3-dicyclohexyl carbodiimide (40 g, 194 mmol) in anhydrous dichloromethane (250 ml). The reaction mixture was stirred at room temperature for 8 hours. The solids were filtered off and dichloromethane distilled off to get crude 49. The crude 49 was purified by column chromatography on silica gel using hexane as eluant to get pure 49 (17 g, 35.1%) as a white powder.

Source