Reaction #2045030

Reaction equation

1,3-dicyclohexyl carbodiimide

(4-nitrophenoxy)acetic acid

(4-Nitro phenoxy)acetic acid

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

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

→

42

Yield 54.0%

(4-Nitro-phenoxy)-acetic acid-2-[2-(4-nitro-phenoxy)-acetoxy]-ethyl ester

Yield 54.0%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   FiltrationThe solids were filtered off
2. 2
   workup.DISTILLATIONdichloromethane distilled off
3. 3
   Otherto get crude 42
4. 4
   OtherThe crude 42 was purified by column chromatography on silica gel

Procedure

To a mixture of (4-nitrophenoxy)acetic acid 40 (80 g, 406 mmol) and (4-nitrophenoxy)acetic acid-2-hydroxyethyl ester 41 (80 g, 332 mmol) in anhydrous dichloromethane (2 L) under nitrogen atm. was added a solution of 1,3-dicyclohexyl carbodiimide (128 g, 620 mmol) in anhydrous dichloromethane (750 ml) drop wise. The reaction mixture was stirred at room temperature for 8 hours. The solids were filtered off and dichloromethane distilled off to get crude 42. The crude 42 was purified by column chromatography on silica gel using hexane:ethyl acetate (95:5) to get pure 42 (75 g, 54%) as a white powder. M.p: 138-139° C.

Source