N-isobutylidene-3-phenoxybenzylamine → 3-Phenoxybenzylidene-isobutylamine

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Reaction Steps

51 g (0.202 mol) of N-isobutylidene-(3-phenoxybenzylamine) is dissolved in 45 ml of dimethyl sulfoxide, and at room temperature (20°-25° C.) is added all at once, with stirring, 2 g (0.0179 mol) of potassium-tert-butylate. The temperature of the reaction solution rises during this addition to 25°-30° C. The solution is stirred for a further hour at room temperature, and is then extracted three times with 50 ml of water each time. The residue is taken up in 30 ml of diethyl ether, dried with magnesium sulfate, and distilled to obtain 48.5 g (0.192 mol) of 3-phenoxybenzylidene-isobutylamine, corresponding to a yield of 95% of theory; b.p. 83° C./4 Pa; nD20 =1.5677.

Provenance & Evidence