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Methyl benzoate is formed by the condensation of methanol and benzoic acid, in presence of a strong acid. [1] [2] Methyl benzoate reacts at both the ring and the ester, depending on the substrate. Electrophiles attack the ring, illustrated by acid-catalysed nitration with nitric acid to give methyl 3-nitrobenzoate.
The phrase ipso nitration was first used by Perrin and Skinner in 1971, in an investigation into chloroanisole nitration. [18] In one protocol, 4-chloro- n -butylbenzene is reacted with sodium nitrite in t -butanol in the presence of 0.5 mol% Pd 2 (dba) 3 , a biarylphosphine ligand and a phase-transfer catalyst to provide 4-nitro- n -butylbenzene.
Since carboxylic acid functional groups are electron withdrawing, during an electrophilic aromatic substitution reaction of nitration, substituents are directed to a meta position which explains this regiochemistry. A less efficient route involves nitration of methyl benzoate, followed by hydrolysis. [3]
It also can be prepared by treating benzaldehyde under nitration conditions, a process that initially converts the aldehyde to the acid. 4-Nitrobenzoic acid is a precursor to 4-aminobenzoic acid , which is in turn used to prepare the anesthetic procaine . 4-Nitrobenzoic acid is prepared by oxidation of 4-nitrotoluene .
The nitration product produced on the largest scale, by far, is nitrobenzene. Many explosives are produced by nitration including trinitrophenol (picric acid), trinitrotoluene (TNT), and trinitroresorcinol (styphnic acid). [3] Another but more specialized method for making aryl–NO 2 group starts from halogenated phenols, is the Zinke nitration.
The inductive and resonance properties compete with each other but the resonance effect dominates for purposes of directing the sites of reactivity. For nitration, for example, fluorine directs strongly to the para position because the ortho position is inductively deactivated (86% para, 13% ortho, 0.6% meta).
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3-Nitrobenzaldehyde is the primary product obtained via the mono-nitration of benzaldehyde with nitric acid. [3] C 6 H 5 CHO + HNO 3 → O 2 NC 6 H 4 CHO + H 2 O. Product distribution is about 19% for the ortho-, 72% for the meta- and 9% for the para isomers.