Sulfuric Acid → 4-(2-Chloroethyl)benzaldehyde

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Reaction Steps

4-(2-Chloroethyl)benzoic acid (2.00 g, 10.83 mmol) was dissolved in THF (40 ml) under an argon atmosphere, and 1M borane-THF complex (16 ml, 16.00 mmol) was slowly added dropwise under ice-cooling. After stirring at room temperature for 2 hours, 1N sulfuric acid (36 ml) was added, and the mixture was stirred for 1 hour and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained crude product was dissolved in dichloromethane (50 ml). Manganese dioxide (10.00 g) was added, and the mixture was stirred overnight at room temperature. After filtration through celite, the filtrate was concentrated under reduced pressure to give the title compound (1.71 g, 91%).

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