tert-Butanol → Isoxazolium, 2-(1,1-dimethylethyl)-5-methyl-, perchlorate (1:1)

Participants

Reaction Steps

1 kg. of 5-methylisoxazole and 892 g. of t-butanol were stirred under nitrogen at 0° C. and 6.37 kg. of 60% perchloric acid were slowly added over a 2 1/2 hour period with vigorous stirring at 0°-5° C. The resulting suspension was allowed to warm to room temperature and stirred overnight. The reaction mixture was then slowly added to a mixture of 20 l. of tetrahydrofuran and 10 l. of ether at 0°-10° C. over a 2 hr. period with stirring. The mixture was then cooled to -5° C. and stirred for an additional 2 hrs. The product (1.821 kg.) was washed well with ether, m.p. 120°-122° C. A second crop (171 g.) was obtained from the mother liquor, m.p. 118°-121° C.

Provenance & Evidence