Acetyl chloride → Diisopropylether methanol

Participants

Reaction Steps

A 3.1 ml (43.4 mmol) portion of acetyl chloride was added to a carbon disulfide suspension (100 ml) of aluminum chloride (11.5 g, 86.7 mmol) and stirred at a room temperature for 30 minutes. Thereto was added dropwise a carbon disulfide solution (150 ml) of 2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one (5.0 g, 28.9 mmol) spending 2 hours. After 2 hours of heating under reflux and confirmation of the disappearance of the material by a thin layer chromatography, this was returned to a room temperature and mixed with isopropyl ether. The supernatant fluid was discarded by decantation, and the remaining rubber-like substance was dissolved in ethyl acetate and washed with water. The water layer was extracted with ethyl acetate, the organic layers were combined and dried (Na2SO4), and then the solvent was evaporated under a reduced pressure. By recrystallizing the thus obtained oily substance from ethyl acetate-isopropyl ether and then from methanol-isopropyl ether, 3.5 g of the title compound was obtained (yield, 56%).

Provenance & Evidence