First of all, the first question: divide the reaction units, benzyl cinnamate = benzyl alcohol+cinnamic acid, cinnamic acid = benzaldehyde+acetic anhydride or ethyl acetate. This led to the design of the reaction route:
A) Benzaldehyde is hydrogenated to obtain benzyl alcohol. Benzaldehyde and ethyl acetate were condensed to obtain ethyl cinnamate, which reacted with benzyl alcohol under alkaline conditions to obtain the target product.
B) Benzyl alcohol is prepared by the same method. Cinnamic acid acetic anhydride was obtained from benzaldehyde and acetic anhydride, and then it was hydrolyzed to cinnamic acid, which was converted into acyl chloride and then reacted with benzyl alcohol.
C) I remember that acetyl chloride can be directly condensed with aromatic aldehydes, so it should be that excess acetyl chloride+benzaldehyde can be catalyzed by trace pyridine to obtain cinnamoyl chloride, and then condensed with benzyl alcohol.
I remember that the experimental manual was B's route. The hydrogenation of benzaldehyde is catalyzed by nickel or platinum. The Perkins reaction catalyst used in condensation to obtain cinnamic acid mixed anhydride is sodium acetate/potassium acetate, and it seems that potassium carbonate can also be used.
I'm not sure which route you want to take, so it's not easy to answer below. One more thing, this should be the landlord's homework problem, and should not be thrown out for others to answer.
As for the device diagram, I won't draw it. I will definitely use round bottom flask, condenser tube and reflux tube. The condensation reaction takes a long time to reflux.
If the separation method is used, the final ester must be washed with weak acid, weak base, brine and water, then dried and distilled. If possible, through the chromatographic column. The separation of intermediate products depends on how you choose the route and what the intermediate products are.