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4-Methylbenzyltrimethylammonium hydroxide

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4-Methylbenzyltrimethylammonium hydroxide
Names
Other names p-Methylbenzyltrimethylammonium hydroxide
Identifiers
CAS Number
3D model (JSmol)
PubChem CID
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-1Key: BHZSLQZBUUWFED-UHFFFAOYSA-M
SMILES
  • .C=1C=C(C=CC1C)C(C)(C)C
Properties
Chemical formula C11H19NO
Molar mass 181.279 g·mol
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 , 100 kPa). Infobox references
Chemical compound

4-Methylbenzyltrimethylammonium hydroxide is a quaternary ammonium compound with the formula C11H18NOH. 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 Paracyclophane.

Synthesis of 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 paracyclo(2,5)thiophenophane).

References

  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
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