A 5-l. three-necked flask is equipped with a high-speed, motor-driven stirrer passing through a bushing in the center neck (Note 1). The side necks are equipped with rubber stoppers each carrying a short length of 8-mm. glass tubing, bent at right angles. A 10–12 in. length of stout, flexible iron wire is passed through one of these pieces of tubing. Two liters of liquid ammonia (Note 2) and 2 g. of ferric nitrate hydrate are placed in the flask. One hundred grams of sodium (4.35 g. atoms) is cut into rectangular pieces about 3 by ¾ by ¾ in. in size. One of the pieces of sodium is hooked onto the lower end of the iron wire and lowered into the liquid ammonia. Stirring is not necessary during this part of the reaction, but it is advisable. When the lump of sodium has reacted, the solution turns from blue to gray, and the remaining pieces of sodium are added in the same manner. The addition requires about 45 minutes (Note 3).

The stopper carrying the iron wire is removed, 2 g. of anil is added, and then 528 g. (2 moles) of finely powdered, dry styrene dibromide is added gradually with vigorous stirring. The addition requires about 1 hour (Note 4). Stirring is continued for 2 hours (Note 5) after the addition has been completed, after which 600 ml. of concentrated ammonium hydroxide is added, followed by 1 l. of distilled water, and the mixture is allowed to stand until the frost on the outside of the flask is entirely melted.

The aqueous solution is then steam-distilled from the same flask (Note 6) until no more oil passes over. This usually requires about 6 hours, and 1.5–2 l. of distillate is collected. The phenylacetylene in the distillate is separated and washed several times with distilled water to remove ammonia (Note 7). The washed material is dried over anhydrous magnesium sulfate and distilled through an efficient column (Note 8) under reduced pressure. Almost the entire product distils at 73–74°/80 mm. The yield is 93–106 g. (45–52%); n_D20 1.5465–1.5484.