Trimethylsilyl cyanide → 5,6-Dimethoxy-3,4-dihydronaphthalene-1-carbonitrile

Participants

Reaction Steps

A solution of 5,6-dimethoxy-1-tetralone (30 g, 0.14 mole), trimethylsilylcyanide (15.8 g, 0.156 mole), ca. 15 mLs dry benzene, and catalytic AlCl3 was stirred under N2 at 70° (oil bath) for 15 hours. Benzene was removed (in-vacuo), 300 mL MeOH was added to the crude product, and the solution was stirred at 0°-10° C. as HCl was bubbled through the solution for 3 hours. Methanol was evaporated (in-vacuo) and ca. 500 mL water was added to the residue. The resultant solid was filtered, washed with water, and dried (under high-vacuum) to yield 29.2 g of yellow solid. (99.8%); M+ 215; mp 139°-40° C.

Provenance & Evidence