Methyl benzoate

Methyl benzoate is an ester with the chemical formula C6H5COOCH3. It is formed by the condensation of methanol and benzoic acid. It is a colorless to slightly yellow liquid that is insoluble with water, but miscible with most organic solvents.

Methyl benzoate has a pleasant smell, strongly reminiscent of the fruit of the feijoa tree, and it is used in perfumery. It also finds use as a solvent and as a pesticide used to attract insects.

However drug searching dogs are trained to detect the smell of methyl benzoate because of its connection to cocaine. Cocaine hydrochloride, though in its purest form odorless, naturally decomposes the benzoyl group on the cocaine molecule from the remnants of chemicals used in processing it, producing methyl alcohol and benzole acid, which stabilize after a short time into methyl benzoate.

It is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.

Reactions of methyl benzoate

 * Electrophilic substitution: Methyl benzoate undergoes nitration with nitric acid in the presence of sulfuric acid, forming methyl 3-nitrobenzoate. This takes place when nitric acid is protonated and forms the NO2+, nitronium cation. This cation is the electrophile and attacks the benzene ring to form methyl 3-nitrobenzoate.


 * Saponification: Methyl 3-nitrobenzoate undergoes saponification with addition of NaOH. The ester is converted into a carboxylic acid.  The result is the sodium salt of the acid, which can be acidified with aqueous HCl to form 3-nitrobenzoic acid.