Reaction #725897

Reaction equation

[2-(4-Nitrophenoxy)-ethoxy]acetic acid methyl ester

→

23

Yield 71.1%

[2-(4-Amino-phenoxy)-ethoxy]-acetic acid methyl ester

Yield 71.1%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   FiltrationThe catalyst was filtered
2. 2
   Concentrationthe filtrate concentrated
3. 3
   workup.ADDITIONhexane (3 ml) added
4. 4
   Filtrationthe solid filtered

Procedure

[2-(4-Nitrophenoxy)-ethoxy]acetic acid methyl ester 22 (1 g, 3.9 mmol) was dissolved in anhydrous ethyl acetate (20 ml), palladium carbon (10%, 0.1 g) added and the mixture stirred under an atmosphere of hydrogen using balloon for 30 minutes. The catalyst was filtered, the filtrate concentrated, hexane (3 ml) added, and the solid filtered to give 23 (625 mg, 70.9%) as a light brown powder. The melting point was found to be 51-52.5° C. The structure was confirmed with IR and NMR.

Source