A. 1-Phenyldialin. A solution of phenylmagnesium bromide is prepared in the usual manner¹ from 11 g. (0.45 gram atom) of magnesium, 75 g. (0.48 mole) of bromobenzene, and 175 ml. of ether. As soon as the metal has reacted, a solution of 58.4 g. (0.4 mole) of α-tetralone in 60 ml. of ether is added from a dropping funnel as rapidly as possible so that vigorous refluxing is maintained; about 30 minutes is required. The reaction mixture is then heated under reflux for an additional 30 minutes and allowed to stand for 1 hour. The magnesium complex is decomposed by about 250 g. of ice and 40 ml. of concentrated hydrochloric acid. The ether layer is separated and distilled with steam to remove impurities (Note 1); about 6 hours is necessary, and approximately 4.5 l. of distillate is collected. The heavy residual oil is separated from the water, and 80 ml. of ether and 10 g. of calcium chloride are added. After 4–5 minutes, the calcium chloride is removed by filtration, and the ether is driven off by distillation on a steam bath. Twenty milliliters of acetic anhydride is then added, and the flask and contents are heated in a steam bath (Note 2) for 20–25 minutes. The mixture is finally distilled under reduced pressure through a 15-in. Widmer column (Note 3). The fraction which boils at 135–140°/2 mm. is collected; the yield is 35–40 g. (42–48%).

B. 1-Phenylnaphthalene. A mixture of 6 g. (0.18 mole) of powdered sulfur and 35 g. (0.17 mole) of 1-phenyldialin in a 200-ml. Claisen flask having a modified side arm is heated for 30 minutes in a metal bath the temperature of which is 250–270° (Note 4). At the end of this time the evolution of hydrogen sulfide will have ceased. The heavy oil (Note 5) is then distilled from the same flask; the yield is 32–33 g. (91–94%); the boiling range of the product is 134–135°/2 mm. or 189–190°/12 mm. (Note 6) and (Note 7)"/>.