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Derivatives of Cerotic Acid.
Cerotanilide.—This compound has not previously been prepared. It was obtained by heating cerotic acid with twice the theoretical quantity of aniline in a sealed tube to a temperature 150° to 170° for four hours. At the expiration of this period the mixture had formed a homogeneous dark soft solid. This was then washed with dilute acetic acid, in order to remove as much free aniline as possible. The anilide thus obtained was then dissolved in alcohol, the solution rendered alkaline with ammonia, and the unchanged cerotic acid precipitated by alcoholic calcium chloride. The filtrate from the insoluble calcium salts deposited the anilide on cooling. It was purified by crystallization from alcohol, acetic acid, and motor spirit.
The anilide thus obtained melted at 98°5° C., and the melting-point was unchanged by further crystallization.
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The anilide is a white solid, fairly soluble in both alcohol and acetic acid, but more so in motor spirit, from which, however, it does not crystallize well.
The crystals from alcohol were large groups of fine needles, joined together in tree-like formation. The yield of the anilide was 55 per cent. of the theoretical.
On one occasion a sample of anilide crystallized from ethyl alcohol commenced to melt at 98°5°, but did not melt completely until a temperature of 118° was reached. After resolidification the sample melted sharply at the lower temperature; and the sample when crystallized from motor spirit also melted sharply at the lower temperature. There can be little doubt, therefore, that this anilide is dimorphous. The only other instance I can find of an anilide exhibiting dimorphism is that of acetanilide.*
[Footnote] * Hans Meyer, “Analyse und Constitutionsermittelung Organ Verbindungen,” p. 47.