Vanillic Acid → 4-(Nitrooxy)butyl 4-hydroxy-3-methoxybenzoate

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To a solution of vanillic acid (5.0 g, 29.73 mmol) in N,N-dimethylformamide (50 ml), cesium carbonate (9.68 g, 29.73 mmol) was added. The reaction was cooled at 0° C. and a 20% solution of 1-bromo-4-(nitrooxy)butane in dichloromethane (29.45 g) was added. The reaction was stirred at room temperature for 69 hours. The mixture was poured into a 5% aqueous NaH2PO4 solution and extracted with diethyl ether (3×70 ml) The organic layers were washed with water (70 ml), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (Biotage System, Cartridge column FLASH 65+M™ KP-Sil, eluent: gradient n-hexane/ethyl acetate 95/5 (500 ml), to n-hexane/ethyl acetate 1/1 during 4000 ml, n-hexane/ethyl acetate 1/1 (500 ml)). The product (5.88 g) was obtained.

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