t-Butyl 3-methyl-4-nitrophenoxyacetate → Tert-butyl 2-(4-amino-3-methylphenoxy)acetate

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Reaction Steps

A solution of 2.35 g (8.8 mmol) of the title A compound, (3-methyl-4-nitrophenoxy)-acetic acid t-butyl ester in 40 mL of EtOH is hydrogenated at 45 psi for 18 h in the presence of 10% Pd/C. The catalyst is removed by filtration through Celite and the filtrate is concentrated to give (4-amino-3-methylphenoxy)-acetic acid t-butyl ester as an oil: 1H-NMR (CDCl3) δ 6.68 (br s, 1H), 6.61 (s, 2H), 4.43 (s, 2H), 2.15 (s, 3H), 1.48 (s, 9H); [M+1]+=238.

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