1. The reaction sometimes takes place with considerable violence and material may be lost through the condenser. Accordingly, a somewhat larger flask is generally desirable, or the upper end of the reflux condenser is provided with a wide tube leading to an empty flask.
2. The procedure described requires 50 per cent of the amount of dilute alcohol which is ordinarily recommended in the literature. This allows one to prepare just double the amount of material in the same sized flask. The product obtained in this way, however, is slightly yellower than that obtained when more alcohol is used, but upon recrystallization it gives just as pure a product as that obtained by recrystallization of crude material made in the presence of more solvent. The results of many experiments lead to the conclusion that, if large amounts of benzoin are to be prepared, the method described above is the better one. If, however, only a small amount is needed and a good grade of crude material is satisfactory, the larger amount of solvent is perhaps more desirable.
3. It is absolutely necessary that pure benzaldehyde be used for this reaction. The crude benzaldehyde which is obtained on the market should be washed with sodium carbonate solution, dried, distilled with minimum atmospheric exposure, and a fraction collected at 178–180°. Crude material will never give much more than a 50 per cent yield of benzoin.
4. Several times when benzoin was being prepared, the condensation took place and was complete after boiling five to ten minutes or even less, the product separating out in the hot solution with evolution of heat. The yield under these conditions was always good and the color better than when the reaction took a longer time. The cause of this occasional rapid reaction was not discovered, but it was probably due to inoculation with a little benzoin in certain of the experiments. When it takes place as just described, the flask and efficient condenser used will be sufficient to condense the sudden, rapid evolution of alcohol vapors caused by the heat of crystallization of the benzoin.