4-Methylbenzyltrimethylammonium hydroxide is a quaternary ammonium compound with the formula C11H18N+OH−. It can be synthesized by reacting 4-methylbenzyl bromide with triethylamine, followed by stirring with silver oxide in water.
Reactions When heated with phenothiazine in toluene, it undergoes Hofmann elimination to form [2.2]Paracyclophane.
Paracycloheterophanes can be obtained by heating it with other quaternary ammonium hydroxides (e.g. with (5-methyl-2-thienylmethyl)trimethylammonium hydroxide to form [2.2]paracyclo(2,5)thiophenophane).Otsubo, T., Mizogami, S., Osaka, N., Sakata, Y., & Misumi, S. (1977). Layered Compounds. XLII. Syntheses and Properties of Layered Paracycloheterophanes. Bulletin of the Chemical Society of Japan, 50(7), 1841–1849.
References