Hydrochloric Acid → 2-Hexanoylthiophene

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Thiophene (0.9 g, 10.7 mmol) and hexanoyl chloride (1.52 g, 11.3 mmol), both of which were obtained from Aldrich and used without further purification, were dissolved in benzene (20 mL) and cooled to 0° C. under argon. Stannic Chloride (10.7 mL, 10.7 mmol, 1 M solution in dichloromethane) was added dropwise and the resulting solution was stirred overnight. (Upon addition of the Stannic Chloride, the color changed from colorless to red.) After stirring overnight, 20 mL of a 50:50 mixture of concentrated hydrochloric acid and water was added. The resulting mixture was stirred for two hours whereupon the color became golden yellow. The organic layer was separated, washed with sodium bicarbonate solution, dried (Na2SO4) and concentrated to yield 2-hexanoylthiophene 2 (1.83 g, 94% yield). The compound was further purified by column chromatography using hexane/dichloromethane as the elutant.

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