2-Methylbenzyltrimethylammonium

This procedure is suitable for the preparation of the following quaternary salts with changes only in the proportion of ethanol employed 2-methylbenzyltrimethylammonium iodide, using 350 ml. of ethanol per mole of amine (yield 98-99%), and 2,3-dimethylbenzyltrimethylammonium iodide, using 500 ml. of ethanol per mole of amine (yield 98-99%). 

Methylbenzylethyldimethylam-monium bromide, 34, 58 2-Methylbenzyltrimethylammonium iodide, 34, 63 Methyl bromide, 38,41 N-Methyl-a-bromo- -butyranilide,... 

Methylbenzyltrimethylammonium bromide is not noticeably hygroscopic. The crude product, after it has been dried at 80° under reduced pressure over phosphorus pentoxide, melts at 197-199°. RecrystaUization from absolute ethanol followed by similar drying gives crystals melting at 199-200°. Less thoroughly dried samples show lower and erratic melting points. 

A. p-Methylbenzyltrimethylammonium bromide. In a 1-1. threenecked flask equipped with a stirrer, a reflux condenser provided with a Drierite drying tube, and a gas inlet tube about 1 cm. above the surface of the liquid are placed 600 ml. of dry ether and 100 g. (0.54 mole) of a-bromo-p-xylene (Note 1). The flask is cooled in an ice-water bath with stirring. A dry, weighed trap... 

Paracyclophane can be prepared by the Hofmann elimination of p-methylbenzyltrimethylammonium hydroxide in the presence of 2-imid-azolidinone as co-solvent and crown ethers, dimethyl sulfoxide (DMSO) and other compounds as reaction promoters. Yields greater than 70% are reported. 

Methoxynaphthalene, 223 p-Methoxyphenol, 99 4-Methoxyphenyl-4-allyloxy benzoate, 537 Methoxyphenylisocyanate, 306 4-Methoxyphenylsulfonyl chloride, 253 Methyl-(4-anilino-phenyl) sulfide, 187, 188 A -(a-Methylbenzyloxy)-2,2,6,6-tetramethylpiperidine, 41 p-Methylbenzyltrimethylammonium hydroxide, 70... 

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