4-Nitrophenol → 1-Nitro-4-(octyloxy)benzene

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Reaction Steps

1-bromooctane (1 g, 5.18 mmole) and 4-nitrophenol, sodium salt (0.92 g, 5.71 mmole) were refluxed in DMSO (30 ml) at 120° C. for 5 hours. The DMSO was distilled off to near dryness. The resulting brown residue was loaded onto a silica column and eluted with 10:1 mixture of petroleum ether and diethylether. The yield was 30%. 1H NMR (CDCl3, peaks at=8.18 (m, 2H), 6.93 (m, 2H), 4.04 (t, 2H), 1.81 (p, 2H), 1.33 (m, 10H), 0.89 (t, 3H). Elemental analysis calculated for C14H21O3N: C, 66.91; H, 8.42; N, 5.57. Found: C, 66.97; H, 8.34; N5.52.

Provenance & Evidence