Methyl benzoate
Encyclopedia
Methyl benzoate is an ester
with the chemical formula
C6H5COOCH3. It is formed by the condensation of methanol
and benzoic acid
, in presence of a strong acid such as hydrochloric acid
. It is a colorless liquid that is poorly soluble in water, but miscible with organic solvents.
, methyl benzoate undergoes nitration
with nitric acid
in the presence of sulfuric acid
to give methyl 3-nitrobenzoate. Methyl benzoate 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
.
tree, and it is used in perfumery. It also finds use as a solvent
and as a pesticide
used to attract insects. 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.
Ester
Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...
with the chemical formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....
C6H5COOCH3. It is formed by the condensation of methanol
Methanol
Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...
and benzoic acid
Benzoic acid
Benzoic acid , C7H6O2 , is a colorless crystalline solid and the simplest aromatic carboxylic acid. The name derived from gum benzoin, which was for a long time the only source for benzoic acid. Its salts are used as a food preservative and benzoic acid is an important precursor for the synthesis...
, in presence of a strong acid such as hydrochloric acid
Hydrochloric acid
Hydrochloric acid is a solution of hydrogen chloride in water, that is a highly corrosive, strong mineral acid with many industrial uses. It is found naturally in gastric acid....
. It is a colorless liquid that is poorly soluble in water, but miscible with organic solvents.
Reactions
Methyl benzoate undergoes reactions both at the ring and the ester. Illustrative of its ability to undergo electrophilic substitutionElectrophilic substitution
Electrophilic substitution reactions are chemical reactions in which an electrophile displaces a group in a compound, typically but not always hydrogen. Electrophilic aromatic substitution is characteristic of aromatic compounds and is an important way of introducing functional groups onto benzene...
, methyl benzoate undergoes nitration
Nitration
Nitration is a general chemical process for the introduction of a nitro group into a chemical compound. The dominant application of nitration is for the production of nitrobenzene, the precursor to methylene diphenyl diisocyanate...
with nitric acid
Nitric acid
Nitric acid , also known as aqua fortis and spirit of nitre, is a highly corrosive and toxic strong acid.Colorless when pure, older samples tend to acquire a yellow cast due to the accumulation of oxides of nitrogen. If the solution contains more than 86% nitric acid, it is referred to as fuming...
in the presence of sulfuric acid
Sulfuric acid
Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...
to give methyl 3-nitrobenzoate. Methyl benzoate also undergoes hydrolysis
Hydrolysis
Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...
with addition of aqueous NaOH to give methanol and sodium benzoate
Sodium benzoate
Sodium benzoate has the chemical formula NaC6H5CO2; it is a widely used food preservative, with E number E211. It is the sodium salt of benzoic acid and exists in this form when dissolved in water. It can be produced by reacting sodium hydroxide with benzoic acid.-Uses:Sodium benzoate is a...
, which can be acidified with aqueous HCl
Hydrochloric acid
Hydrochloric acid is a solution of hydrogen chloride in water, that is a highly corrosive, strong mineral acid with many industrial uses. It is found naturally in gastric acid....
to form benzoic acid
Benzoic acid
Benzoic acid , C7H6O2 , is a colorless crystalline solid and the simplest aromatic carboxylic acid. The name derived from gum benzoin, which was for a long time the only source for benzoic acid. Its salts are used as a food preservative and benzoic acid is an important precursor for the synthesis...
.
Odor
Methyl benzoate has a pleasant smell, strongly reminiscent of the fruit of the feijoaFeijoa
Acca sellowiana, a species of flowering plant in the myrtle family, Myrtaceae, is native to the highlands of southern Brazil, Colombia, Uruguay, and northern Argentina. It is widely cultivated as a garden plant and fruiting tree in New Zealand, and can be found as a garden plant in Australia and...
tree, and it is used in perfumery. It also finds use as a solvent
Solvent
A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature...
and as a pesticide
Pesticide
Pesticides are substances or mixture of substances intended for preventing, destroying, repelling or mitigating any pest.A pesticide may be a chemical unicycle, biological agent , antimicrobial, disinfectant or device used against any pest...
used to attract insects. 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
Cocaine
Cocaine is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. The name comes from "coca" in addition to the alkaloid suffix -ine, forming cocaine. It is a stimulant of the central nervous system, an appetite suppressant, and a topical anesthetic...
hydrochloride
Hydrochloride
In chemistry, hydrochlorides are salts resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base . This is also known as muriate, derived from hydrochloric acid's other name: muriatic acid....
hydrolyzes in moist air to give methyl benzoate; drug-sniffing dogs are thus trained to detect the smell of methyl benzoate.