This is a very famous and classic organic chemistry experiment. In fact, there are standard answers, and you should look for the original experiment manual to find the answer.

First question: Divide the reaction units, benzyl cinnamate = benzyl alcohol + cinnamic acid, and cinnamic acid = benzaldehyde + acetic anhydride or ethyl acetate. The reaction route design is derived from this:

a) Benzaldehyde is hydrogenated to obtain benzyl alcohol. Benzaldehyde and ethyl acetate are condensed to obtain ethyl cinnamate, and ethyl cinnamate undergoes a transesterification reaction with benzyl alcohol under alkaline conditions to obtain the target product.

b) Prepare benzyl alcohol in the same way. Benzaldehyde and acetic anhydride are used to obtain cinnamic acid acetic acid mixed anhydride, which is then hydrolyzed to obtain cinnamic acid. The cinnamic acid is converted into acid chloride and then reacted with benzyl alcohol.

c) I remember that acetyl chloride can directly condense with aromatic aldehydes, so it should be that excess acetyl chloride + benzaldehyde is catalyzed by trace amounts of pyridine to obtain cinnamoyl chloride, which is then condensed with benzyl alcohol.

I remember that the experiment manual in the past was route B. The conditions for hydrogenation of benzaldehyde are nickel or platinum catalysis. The Perkins reaction catalyst used in the condensation to obtain cinnamic acid mixed anhydride is sodium/potassium acetate, and it seems that potassium carbonate can also be used.

I'm not sure which route you want to use, so it's hard to answer below. Another one, this should be the poster's homework question. You shouldn't just throw it out and let others answer it.

As for the device diagram, I will not draw it. A round-bottomed flask, condenser tube, and reflux tube must be used. The condensation reaction requires reflux for a long time.

In terms of separation methods, the final ester must be washed with weak acid, weak alkali, brine, water, and then dried and distilled. If possible, pass through the column. The separation of intermediate products depends on how you choose the route and what the intermediate products are.