Reaction #2045045

Reaction equation

2-(4-nitrophenoxy)ethoxyacetic acid methyl ester

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

→

60

Yield 71.1%

2-(4-Aminophenoxy)ethoxyacetic acid methyl ester

Yield 71.1%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Otherfor 30 min
2. 2
   FiltrationCatalyst was filtered
3. 3
   Concentrationfiltrate concentrated
4. 4
   workup.ADDITIONhexane (3 ml) added
5. 5
   Filtrationthe solid filtered

Procedure

2-(4-nitrophenoxy)ethoxyacetic acid methyl ester 59 (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 a hydrogen atm. using a balloon for 30 min. Catalyst was filtered, filtrate concentrated, hexane (3 ml) added, and the solid filtered to give 60 (625 mg, 70.9%) as a light brown powder. M.p: 51-52.5° C.

Source