4-Methylbenzyltrimethylammonium hydroxide explained

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.^[1]

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).^[2]

Notes and References

1. 10.15227/orgsyn.042.0083. [2.2]Paracyclophane . Organic Syntheses . 1962 . 42 . 83. H. E. Winberg, F. S. Fawcett .
2. 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.