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In a dry flask fitted with a ground-in condenser and protected from moisture were placed 33.0 g. (0.16 mole) of bromonaphthalene, b. p. 153—154° at 11 mm., 17.3 g. (0.19 mole) of cuprous cyanide, and 20 cc. of pyridine (dried over barium oxide). The mixture was heated at 220° for fifteen hours, and the resulting brown solution poured into dilute ammonia in a separatory funnel. After vigorous shaking for several minutes, the nitrile was extracted with ether and the extract washed successively with dilute ammonia, water, dilute hydrochloric acid, water, and saturated sodium chloride solution. After the first treatment with ammonia it was usually necessary to remove some dark insoluble matter by filtration as this seriously interfered with separation of the layers. The ether was removed and the residue vacuum distilled. The temperature rose abruptly to the boiling point and the yield of colorless nitrile, b. p. 173—174° at 27 mm., was 22.8 g., or 93%. This material had a melting point of 34—35° and on hydrolysis with sulfuric acid-acetic acid-water yielded pure 1-naphthoic acid, m. p. and mixed m. p. 162—163°.
In an experiment similar to the above, 18.1 g. of 1-chloronaphthalene, b. p. 144—146.5° at 29 mm., 12.0 g. of cuprous cyanide and 10 cc. of pyridine were heated at 245—250° (temperature of bath) for twenty-four hours. The yield of 1-naphthonitrile was 15.6 g., or 92%. In an experiment in which the heating period was only six hours, the yield was 70%, a fore run of unreacted 1-chloronaphthalene being obtained.
© Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru