Hydrochloric Acid → 2-Hexanoylthiophene

Temperature

0 °C

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.

1. customThe 2-hexanoyl thiophene was prepared
2. customused without further purification, in benzene (20 mL)
3. additionwas added
4. stirringThe resulting mixture was stirred for two hours whereupon the color
5. customThe organic layer was separated
6. washwashed with sodium bicarbonate solution
7. customdried (Na2 SO4)
8. concentrationconcentrated

ORD record

ord-3a490ef105df41c38edeff761f875b33

Source dataset

uspto-grants-1998_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05736592