Systematic Method of Benzalaniline

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Benzalaniline (CAS NO.: 538-51-2), which is also known as Aniline, N-benzylidene-, could be produced through the following synthetic routes.

In a 500-cc. three-necked, round-bottomed flask provided with a mechanical stirrer is placed 106 g. (1 mole) of benzaldehyde, and 93 g. (1 mole) of aniline is added with rapid stirring. After a few seconds a reaction occurs with evolution of heat and separation of water. The mixture is allowed to stand fifteen minutes and is then poured, with vigorous stirring, into 165 cc. of 95 per cent alcohol in a 600-cc. beaker. Crystallization begins in about five minutes, and the mixture is allowed to stand, first ten minutes at room temperature, and then thirty minutes in ice water. The almost solid mass is next transferred to a large Büchner funnel, filtered by suction, pressed out, and air-dried. The yield of pure benzalaniline melting at 52° is 152–158 g. (84–87 per cent of the theoretical amount).

By concentrating the mother liquor to about one-half of its original volume at room temperature or lower, under reduced pressure by means of a water pump, an additional 10 g. of benzalaniline may be obtained. This is of good quality and melts at 51°.