How can I make benzyl benzoate?

Question

Benzyl Benzoate is obtain by mixing Benzyl Alcohol and Benzoic acid, right? what are the proportion to mix them and get Benzyl Benzoate ?

Answer 1

Ideally 1 molar equivalent of each gives you the product using acidic catalysis (resin, sulfuric acid) in the heat.
Practically you can use the alcohol as solvent and distill the mixture after removal of the catalyst by filtration or washing with diluted caustic.
You can also use an inert solvent (e.g.toluene) and a slight excess of benzoic acid. This excess will be removed with the washing as above. Then you have to distill again.
Advantage of the latter procedure lower boiling point of the solvent => easier to get rid of it.

Answer 2

Benzyl benzoate is the organic compound with the formula C6H5CH2O2CC6H5. This easily prepared compound has a variety of uses.

Synthesis
This colourless liquid is formally the condensation product of benzoic acid and benzyl alcohol. It can also be generated from benzaldehyde by the Tishchenko reaction.

2 C6H5CHO → C6H5CH2O2CC6H5

The Tishchenko reaction is a chemical reaction that involves disproportionation of an aldehyde lacking a hydrogen atom in the alpha position in the presence of an alkoxide. The reaction product is an ester. Catalysts are aluminium alkoxydes or sodium alkoxides. Benzaldehyde reacts with sodium benzyloxide (generated from sodium and benzyl alcohol) to benzyl benzoate.


Paraformaldehyde reacts with boric acid to methyl formate. The key step in the reaction mechanism for this reaction is a 1,3-hydride shift in the hemiacetal intermediate formed from two successive nucleophilic addition reactions, the first one from the catalyst. The hydride shift regenerates the alkoxide catalyst.