The Synthesis and Purification of Aromatic Hydrocarbons. 3 - Isobutylbenzene Sec-Butylbenzene
AIRCRAFT ENGINE RESEARCH LAB CLEVELAND OH
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The syntheses of isobutylbenzene, sec-butylbenzene, and tert-butylbenzene in 11-gallon quantities are described. The sec-butylbenzene was prepared by reacting sec-butyl alcohol with benzene in the presence of aluminum chloride and anhydrous hydrogen chloride. The tert-butylbenzene was prepared in a similar manner without the use of hydrogen chloride. The preparation of isobutylbenzene involved the reaction of phenylmagnesium bromide with methallyl chloride to yield 2-methyl-3-phenyl-1-propene, which was partly rearranged to 2-methyl-1-phenyl-1-propene. Both olefins were isolated. The physical properties are tabulated and freezing curves are plotted for the five hydrocarbons.
- Organic Chemistry