4-Methylbenzyltrimethylammonium hydroxide

4-Methylbenzyltrimethylammonium hydroxide
Names
	Other names p-Methylbenzyltrimethylammonium hydroxide
Identifiers
CAS Number	43011-61-6 ;
3D model (JSmol)	Interactive image;
PubChem CID	12324565;
	InChI InChI=1S/C11H18N.H2O/c1-10-5-7-11(8-6-10)9-12(2,3)4;/h5-8H,9H2,1-4H3;1H2/q+1;/p-1 Key: BHZSLQZBUUWFED-UHFFFAOYSA-M;
	SMILES [OH-].C=1C=C(C=CC1C)C[N+](C)(C)C;
Properties
Chemical formula	C11H19NO
Molar mass	181.279 g·mol−1
Boiling point	dec.
Related compounds
Related compounds	Benzyltrimethylammonium hydroxide
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.^[1]

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]

References

^ ^a ^b H. E. Winberg, F. S. Fawcett (1962). "[2.2]Paracyclophane". Organic Syntheses. 42: 83. doi:10.15227/orgsyn.042.0083.
^ 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. doi:10.1246/bcsj.50.1841

[OrgSyn-1] H. E. Winberg, F. S. Fawcett (1962). "[2.2]Paracyclophane". Organic Syntheses. 42: 83. doi:10.15227/orgsyn.042.0083.

[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. doi:10.1246/bcsj.50.1841

[1]

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