Reaction #2045033

Reaction equation

(4-Aminophenoxy)acetic acid methyl ester

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

→

46

Yield 22.8%

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

Yield 22.8%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   OtherThe catalyst was removed by filtration, ethyl acetate
2. 2
   workup.DISTILLATIONwas distilled off
3. 3
   workup.ADDITIONhexane was added
4. 4
   FiltrationThe solid product was filtered
5. 5
   Otherdried

Procedure

(4-Aminophenoxy)acetic acid methyl ester 41 (1 g, 4.15 mmol) was dissolved in ethyl acetate in a pressure vessel, palladium on carbon (5%, 0.5 g) was added and the mixture was stirred under an atmosphere of hydrogen (0.5 Kg) for one hour. The catalyst was removed by filtration, ethyl acetate was distilled off and hexane was added. The solid product was filtered and dried to give pure 46 (0.2 g, 22.8%) as a brown powder. M.p: 104-106.3° C.

Source