Ammonia → 4-(Benzyloxy)-2-methylaniline

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Reaktionsschritte

A solution of 4-benzyloxy-2-methyl nitrobenzene (6.4 mmol, 1.5 g) and sodium hydrosulfite (16 mmol, 2.2 g) in 140 mL of MeOH/water (2:1) was refluxed for two hours. Upon cooling, the solution was poured into 500 mL of aqueous ammonia and the product extracted into CH2Cl2 (4×). The organic layer was washed with water, brine and dried over Na2SO4, filtered and concentrated to provide 4-benzyloxy-2-methylaniline (0.47 g, 51%) as a light brown oil. 1H NMR (300 MHz, CDCl3) δ:7.4 (m, 5 H), 6.76 (d, J=2.1 Hz, 1 H), 6.70 (dd, J=7.2, 2.1 Hz, 1 H), 6.61 (d, J=7.2 Hz, 1 H), 4.98 (s, 2 H), 2.15 (s, 3 H).

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