Methylparaben → Methyl 4-(2-quinolinylmethoxy)benzoate

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To a solution of 2-Chloromethyl quinoline. (2 g, 9.3 mmole) in acetone (47 ml, 0.2M) was added 4-hydroxy benzoic acid methyl ester (1.42 g, 1.0 eq.) and potassium carbonate (3.86 g, 3 eq.). The reaction mixture was heated at 60° C. for 16 h under N2 atmosphere, cooled to ambient temperature and poured into 1N sodium hydroxide (50 ml)/ethyl acetate (100 ml). The layers were separated and the organic layer dried magnesium sulfate, filtered and concentrated. Biotage MPLC was run using a 5-30% ethyl acetate/hexane gradient on a 40 M column to provide the title compound as a white solid (1.66 g, 61%). 1H NMR (400 MHz, CDCl3) δ 8.18 (d, J=8.7 Hz, 1 H), 8.07 (d, J=8.3 Hz, 1 H), 7.95 (M, 2H), 7.82 (d, J=7.9 Hz, 1 H), 7.74 (dt, J=7.1, 1.7 Hz, 1 H), 7.62 (d, J=8.3 Hz, 1 H), 7.55 (dt, J=7.9, 1.2 Hz, 1 H), 7.03 (d, J=9.1, 2 H), 5.41 (s, 2 H), 3.84 (s, 3 H); MS: (M+H m/z=294.2).

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