Hydrochloric Acid → 2-Hexanoylthiophene

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The 2-hexanoyl thiophene was prepared by dissolving thiophene (0.9 g, 10.7 mmol) and hexanoyl chloride (1.52 g, 11.3 mmol), both of which were obtained from Aldrich Chemical Supply and used without further purification, in benzene (20 mL). The solution was cooled to 0° C. under argon. Stannic chloride (10.7 mL, 10.7 mmol, 1M solution in dichloromethane) was added dropwise and the resulting solution was stirred overnight. The next day, 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 (Na2 SO4) and concentrated to yield 2-hexanoyl thiophene (94% yield). The compound was further purified by column chromatography using hexane/dichloromethane as the elutant.

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