Benzyl Alcohol → 4-(Benzyloxy)-3-nitropyridine

Participants

Reaction Steps

4-chloro-3-nitropyridine (30 g, 0.19 mol) was slowly added to a suspension of phenylmethanol (30 mL, 0.29 mol), K2CO3 (26.2 g, 0.19 mol and KOH (42.5 g, 0.76 mmol) in toluene (2 L) at 0° C. A catalytic amount of tris[2-(2-methoxyethoxyl)ethyl]amine was added to the reaction mixture, which was then stirred at room temperature for 2 hours. After filtration, the resulting filtrate was concentrated to give the crude product, which was crystallized from DCM/PE (1:5) to afford 4-(benzyloxy)-3-nitropyridine (27.3 g, yield: 62.7%). 1H-NMR (CDCl3, 400 MHz) δ 9.00 (s, 1H), 8.56 (d, J=6.0 Hz, 1H), 7.34˜7.43 (m, 5H), 7.03 (d, J=6.0 Hz, 1H), 5.29 (s, 2H). MS (M+H)+: 231.

Provenance & Evidence