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Both 2-Nitrobenzoic acid and 4-Nitrobenzoic acid are produced as side products, with yields of approximately 20% and 1.5% respectively. [2] 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 ...
2-Nitrobenzoic acid is prepared by oxidation of 2-nitrotoluene. 3-Nitrobenzoic acid is a precursor to 3-aminobenzoic acid, which in turn is used to prepare some dyes. It can be prepared by nitration of benzoic acid. It also can be prepared by treating benzaldehyde under nitration conditions, a process that initially converts the aldehyde to the ...
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.
3,5-dinitrobenzoic acid is obtained from benzoic acid by the nitration reaction with nitric acid in the presence of concentrated sulfuric acid. [1] [2] The nitration can also be started with 3-nitrobenzoic acid, which leads to yields of approximately 98 %. [3]
This intermediate collapses with the elimination of the azo group to yield an aryldiazene with an ortho carboxylate group, which extrudes nitrogen gas to afford the anionic form of the observed benzoic acid product, presumably through the generation and immediate protonation of an aryl anion intermediate. The product is isolated upon acidic workup.
2-Nitrobenzoic acid or o-nitrobenzoic acid is an organic compound with the formula C 6 H 4 (NO 2)CO 2 H. It is prepared by oxidation of 2-nitrotoluene with nitric acid. [1] In consists of a carboxylic acid group and a nitro group in the ortho configuration. Reduction of the nitro group into an amine produces anthranilic acid.
Also in nitration of the nitration of 3-bromobenzoic acid 5-bromo-2-nitrobenzoic acid (83%yield) was obtained as major product and 3-bromo-2-nitrobenzoic acid (13% yield) as minor. On an interesting note the potential isomer 3-bromo-4-nitrobenzoic acid was not detected. [6]
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.