Water → 3-Amino-2,6-di-tert-butylphenol

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Reaction Steps

NaBH4 (433 mg, 11.45 mmol) was added to a solution of 2,6-di-tert-butyl-3-nitrophenol (950 mg, 3.780 mmol) and NiCl2 (1.24 g, 9.568 mmol) in methanol (15 mL) at −15° C. After the addition was complete, the reaction mixture was stirred for 20 seconds and water was added immediately and the reaction mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4 and evaporated in vacuo to afford 3-amino-2,6-di-tert-butyl-phenol (650 mg, 78%). 1H NMR (300 MHz, CDCl3) δ 6.92 (d, J=8.4 Hz, 1H), 6.24 (d, J=8.4 Hz, 1H), 5.39 (s, 1H), 1.62 (s, 9H), 1.39 (s, 9H); MS (ESI) m/z: 222.2 [M+H+].

Provenance & Evidence