Sodium Cyanide → 1-Naphthalenecarbonitrile, 3,4-dihydro-6-methoxy-

Participants

Reaction Steps

A mixture of 25.25 g of dry aluminum chloride, 16.7 g of sodium cyanide, 1.7 g of tetrabutylammonium bromide, and 20 drops of concentrated HCl in 170 mL of nitrobenzene was stirred for two hours under a nitrogen atmosphere. Then 30 g of 6-methoxytetralone was added, and the reaction mixture was stirred at 90° C. for six hours to form 6-methoxy-1-cyano-3,4-dihydronaphthalene. A 200-mL portion of 20% NaOH was added, and the reaction mixture became warm and was stirred vigorously at 60° C. for one hour. The phases were allowed to separate. After the nitrobenzene phase had been transferred to another vessel, 35 g of bromine was slowly added and a precipitate formed. The reaction mixture was then heated to remove any HBr, cooled, and worked up to provide 28 g of 6-methoxy-5-bromo-1-cyanonaphthalene.

Provenance & Evidence