Phosphorus oxychloride → 5-Methoxy-3,4-dihydronaphthalene-1-carbonitrile

Participants

Reaction Steps

A solution of 5-methoxy-1-tetralone (52.0 g, 0.29 mole, Aldrich), TMSCN (51 mL, 0.38 mole, Aldrich), 40 mL dry benzene, and catalytic AlCl3 was stirred under N2 at 65° C. for 1 hour. The reaction mixture was cooled and evaporated to dryness. To the residue was added 300 mL pyridine and POCl3 (80 mL, 0.88 mole). The reaction mixture was stirred at reflux for 2 hours, then was cooled to room temperature and was poured onto ice/concentrated HCl. A precipitate was collected, washed with water, and purified by column chromatography (silica gel/CH2Cl2) to obtain 54 g (73%); M+ 185.

Provenance & Evidence