Formula C8H8O2 Melting point -15 °C | Molar mass 136.15 g/mol Density 1.08 g/cm³ | |
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Methyl benzoate is an organic compound. It is an ester with the chemical formula C6H5CO2CH3. It is a colorless liquid that is poorly soluble in water, but miscible with 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 such as orchid bees.
Contents
Synthesis of methyl benzoate
Synthesis and reactions
Methylbenzoate is formed by the condensation of methanol and benzoic acid, in presence of a strong acid such as hydrochloric acid. It reacts both at the ring and the ester. Illustrative of its ability to undergo electrophilic substitution, methyl benzoate undergoes acid-catalysed nitration with nitric acid to give methyl 3-nitrobenzoate. It also undergoes hydrolysis with addition of aqueous NaOH to give methanol and sodium benzoate, which can be acidified with aqueous HCl to form benzoic acid.
Occurrence
Methyl benzoate can be isolated from the freshwater fern Salvinia molesta. It is one of many compounds that is attractive to males of various species of orchid bees, which apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.
Cocaine hydrochloride hydrolyzes in moist air to give methyl benzoate; drug-sniffing dogs are thus trained to detect the smell of methyl benzoate.
