Step 2. Synthesis of 4-(4-methoxyphenoxy)aniline
To a solution of 1-methoxy-4-(4-nitrophenoxy)benzene (12.0 g, 49 mmol) in ethyl acetate (EtOAc, 250 mL) was added 5% Pt/C catalyst (1.5 g). The resulting suspension was reacted by shaking under hydrogen atmosphere (50 psi) for 18 hours. Upon completion of the reaction, the reaction mixture was filtered through a diatomaceous earth (Celite) pad to remove the catalyst. The filtrate was concentrated under reduced pressure to give an oily product, which gradually solidified on standing (10.6 g, 100% yield). The product was characterized by 1H-NMR (CDCl3): δ 3.54 (broad single peak, 2H), 3.78 (single peak, 3H), 6.65 (double peak, J = 8.8 Hz, 2H), 6.79-6.92 (multiple peaks, 6H); EI-MS m/z 215 (M+).
