Dimethylformamide → Benzoic acid 3,5-dimethyl-benzyl ester

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A mixture of 3,5-dimethylbenzyl bromide (2, 39.8, 0.2M) and sodium benzoate (34.56 g, 0.24M) in anhydrous DMF (400 ml) was stirred at room temperature for overnight. The mixture was then partitioned between ether and water. The organic layer was taken, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give a pale yellow oil. The crude product was purified by silica gel column chromatography (eluent, hexane) to afford 32 g (71%) of a colorless oil. 1H NMR (200 MHz, CDCl3) δ 2.33 (6H, s), 5.29 (2H, s), 6.98 (1H, s), 7.05 (2H, s), 7.38-7.59 (3H, m), 8.05-8.11 (2H, m).

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