Reaction #2045031

Reaction equation

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

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

→

43

Yield 78.0%

(4-Amino-phenoxy)-acetic acid-2-[2-(4-amino-phenoxy)-acetoxy]-ethyl ester

Yield 78.0%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   OtherThe catalyst was removed by filtration and ice water (2.5 L)
2. 2
   workup.ADDITIONwas added to the filtrate
3. 3
   FiltrationCrude 43 was filtered off
4. 4
   Otherdried
5. 5
   Otherrecrystallised in a mixture of methanol:chloroform (1:1)

Procedure

(4-nitro-phenoxy)-acetic acid-2-[2-(4-nitrophenoxy)acetoxy]ethyl ester 42 (100 g, 238 mmol) was dissolved in dry dimethylformamide (500 ml) in a pressure vessel, palladium on carbon (5%, 22 g) added, and the mixture stirred under an atmosphere of hydrogen (4 Kg) for 6 hours. The catalyst was removed by filtration and ice water (2.5 L) was added to the filtrate. Crude 43 was filtered off, dried and recrystallised in a mixture of methanol:chloroform (1:1) to give pure 43 (65 g, 78%) as a light brown shining powder. M.p: 124-125.8° C.

Source