6-Methoxy-alpha-tetralone → 1-Naphthalenecarbonitrile, 3,4-dihydro-6-methoxy-

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Reaction Steps

To a refluxing benzene solution (60 ml) of 6-methoxy-1-tetralone was added trimethylsilyl cyanide (TMSCN) (67.5 g) and a trace of AlCl3 or ZnI2. Refluxing was continued for 1 hr., then the solvent removed under vacuum. Isopropyl alcohol saturated with HCl(g) was added and the solution refluxed for 1 hr. Precipitation began to occur and the reaction was cooled, then evaporated to dryness. Water was added, followed by an ethyl acetate (EtOAc) extraction. The organic layer was washed in sequence with 1 N NaOH, IN HCl, and brine, separated, dried (MgSO4), filtered and evaporated. The dark oil was chromatographed on silica gel and eluted with CH2Cl2, affording 98.5 g, 94% yield of product.

Provenance & Evidence