Phenyl t-Butyl ether (CAS NO.: ), which is also known as Ether, tert-butyl phenyl, could be produced through the following synthetic routes.

A 1-l., three-necked, round-bottomed flask equipped with a sealed mechanical stirrer, a reflux condenser, and a 500-ml. pressure-equalized dropping funnel is arranged for conducting a reaction in an atmosphere of nitrogen by fitting into the top of the condenser a T-tube attached to a low-pressure supply of nitrogen and to a mercury bubbler. The flask is dried by warming with a soft flame as a slow stream of nitrogen is passed through the system. In the cooled flask a solution of phenylmagnesium bromide is prepared from 13 g. (0.53 g. atom) of magnesium turnings, 79 g. (0.5 mole, 53.6 ml.) of bromobenzene, and 200 ml. of anhydrous ether.

After the preparation of phenylmagnesium bromide is complete, the ethereal solution is cooled in an ice bath and 200 ml. of anhydrous ether is added. A solution of 58.3 g. (0.3 mole, 56 ml.) of t-butyl perbenzoate in 120 ml. of anhydrous ether is added, dropwise, with stirring over a 30-minute period, and the stirring is continued for an additional 5 minutes.

The reaction mixture is poured carefully into a cold solution of 40 ml. of concentrated hydrochloric acid in 1 1. of water. The ethereal layer is separated, and the aqueous layer is extracted twice with 150-ml. portions of ether. The combined organic layers are extracted with three 25-ml. portions of 2M sodium hydroxide solution, washed with water until the washings are neutral, and then dried over anhydrous magnesium sulfate. The dried solution is concentrated and the product distilled under reduced pressure, b.p. 57–59°/7 mm. The yield of phenyl t-butyl ether is 35–38 g. (78–84%), n²⁵D 1.4870–1.4880. This synthetic process is applicable to the preparation of other t-butyl ethers.