Feri-Butyl chloride

In a 250 ml. separatory funnel place 25 g. of anhydrous feri.-butyl alcohol (b.p. 82-83°, m.p. 25°) (1) and 85 ml. of concentrated hydrochloric acid (2) and shake the mixture from time to time during 20 minutes. After each shaking, loosen the stopper to relieve any internal pressure. Allow the mixture to stand for a few minutes until the layers have separated sharply draw off and discard the lower acid layer. Wash the halide with 20 ml. of 5 per cent, sodium bicarbonate solution and then with 20 ml. of water. Dry the preparation with 5 g. of anhydrous calcium chloride or anhydrous calcium, sulphate. Decant the dried liquid through a funnel supporting a fluted Alter paper or a small plug of cotton wool into a 100 ml. distilling flask, add 2-3 chips of porous porcelain, and distil. Collect the fraction boiling at 49-51°. The yield of feri.-butyl chloride is 28 g. 

In a thoroughly dry 500-ml., three-necked, round-bottomed flask fitted with a mechanical stirrer, dropping funnel, and a Y-tube containing a caldum chloride drying tube and a thermometer (Note 1) are placed 24.2 g. (26 ml., 0.20 mole) of a-phenyl-ethylamine (Note 2) and 50 ml. of dry benzene (Note 3). The solution is cooled in an ice-salt bath to 5°, and a solution of 44.5 g. (50 ml., 0.41 mole) of feri-butyl hypochlorite2 (Note 4) in 50 ml. of dry benzene (Note 3) is added at such a rate as to maintain the temperature below 10° (Note 5). After the addition of the tert-butyl hypochlorite solution is complete, the reaction mixture is stirred at room temperature 1-4 hours (Note 6). 

The method presented is essentially that described by Lawesson and Yang.2 Phenyl tert-butyl ether has been prepared by acid-catalyzed condensation of isobutylene and phenol3 and by reaction of diphenyliodonium chloride with potassium feri-butoxide.4... 

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