Methanol → 3-Allyloxybenzamide

Participants

Reaction Steps

To 3-hydroxybenzamide (274 mg; 2.0 mM) under a nitrogen atmosphere was added potassium carbonate (276 mg; 21.0 mM). This was dissolved in acetonitrile (20 ml) containing allyl bromide (169 ul; 2.0 mM). The mixture was refluxed for 5 hours, and the reaction followed by T.L.C.: 10% MeOH: 90% CH2Cl2. The excess solvent was then removed under vacuum, the organics extracted into dichloromethane, dried, and the solvent removed, to yield a white solid. This was recrystallised from hot water to produce a white "needle" solid (63%) as the final product. Melting point: 116-117° C. 1H NMR: δ=4.7(m;2H:He,Hf); 5.5(m;2H;Hh,Hi); 6.2(m;1H;Hg); 7.2(m;1H;Hd); 7.6m;4H;Ha,Hb,Hc,NH); 8.1(s;1H;NH). 13C NMR: δ=68.580, 113.821, 117.978, 129.661, 133.893, 136.025, 158.371, 167.892. Mass spectra: EI: 177 (M+); 41 (100%)

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