Synthesis and Characterization of Benzofuranone and its Derivatives

In this experiment a mixture of salicylaldehyde (2 mmol), 4-chlorophenacyl bromide (2 mmol) and potassium tertiary butoxid (T-BuOK) (2mmol) in 10ml of Dichlorometane (DCM), containing molecular sieves was reflexed at 30C^°for 3 hours. Progress of the reaction was monitored by Thin layer chromatography (TLC) using hexane: ethyl acetate (8:2) mixture as mobile phase. After the completion of the reaction, the reaction mixture was washed with 10 % HCl solution followed by water. The organics were dried over anhydrous sodium sulfate. The yellow solid was obtained disolventizing in a rotary evaporator at room temperature affords benzofuran-2-yl (4-chlorophenyl) methanone. Benzofuranone (0.60 ml, 5 mmol) with substituted anilines (5 mmol) in round bottom flasks was refluxed in 15 ml methanol at 40C^° for 3 hours in the presence of 1.5 ml glacial acetic acid. In each case, the precipitated base was filtered off, recrystallized from absolute ethanol and dried in vacuum desiccators. The (Z)-N-(benzofuran-2-yl (4-chlorophenyl) methylene) aniline was obtained.