1-Bromohexane → 4-Hexyloxy-3-methoxybenzonitrile

Beteiligte Stoffe

Reaktionsschritte

To a suspension of sodium hydride, 60% dispersion in oil,(4.8 g; 0.11 mol) in 40 mL of DMF, a solution of 4-hydroxy-3-methoxy-benzonitrile (14.9 g; 0.1 mol) in DMF (40 mL) was added dropwise over 10 minutes. After addition, the reaction mixture was stirred at ambient temperature for 30 minutes, then bromohexane (16.5 g; 0.1 mol) in DMF (20 mL) was added. The reaction mixture was stirred at ambient temperature for 18 hours. The DMF containing reaction mixture was concentrated to a residue, and H2O (100 mL) was added to the residue. The solid was collected by filtration to obtain 8.2 g (35% yield) of the tide compound as white solid. 1H-NMR (DMSO-d6; 200 MHz) δ7.45 (s, 1H), 7.42 (s, 1H), 7.1 (d, 1H), 4.0 (t, 2H), 3.8 (s, 3H), 1.6-1.8 (m, 2H), 1.2-1.5 (m, 8H), and 0.9 ppm (t, 3H).

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