Benzyl Alcohol → p-(Benzyloxy)nitrobenzene

Participants

Reaction Conditions

Reaction Steps

Benzyl alcohol (2.22 g, 20 mmol) was added to a slurry of hexane-washed NaH (60% oil suspension, 820 mg, 20.5 mmol) in DMSO (20 mL), stirred under nitrogen at 20° C., producing strong gas evolution. After 30 minutes, 1-fluoro-4-nitrobenzene (2.826 g, 20 mmol) was added dropwise to the light grey slurry. The reaction mixture became a bright orange red and quite strongly exothermic, and a lot of gas was evolved. After 2 hours, the reaction mixture was poured onto ice-water (200 mL), and the solid was collected by Buchner filtration, rinsed with water (2×50 mL), and air dried to give 1-benzyloxy-4-nitrobenzene (4.188 g, 91.3%) as canary yellow crystals. 1H NMR (DMSO-d6): δ8.16 (2 H, AA'BB', J=9.3 Hz), 7.47 (2 H, d, J=7.1 Hz), 7.41 (2 H, t, J=7.3 Hz), 7.36 (1 H, t, J=7.1 Hz), 7.23 (2 H, AA'BB', J=9.1 Hz), 5.26 (2 H, s).

Provenance & Evidence