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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 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.
3-Nitrobenzoic acid is an organic compound with the formula C 6 H 4 (NO 2)CO 2 H. It is an aromatic compound and under standard conditions, it is an off-white solid. The two substituents are in a meta position with respect to each other, giving the alternative name of m-nitrobenzoic acid.
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.
Substance Formula 0 °C 10 °C 20 °C 30 °C 40 °C 50 °C 60 °C 70 °C 80 °C 90 °C 100 °C Barium acetate: Ba(C 2 H 3 O 2) 2: 58.8: 62: 72: 75: 78.5: 77: 75
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.
Raney nickel, platinum on carbon, or zinc dust and formic acid or ammonium formate [6] α,β-Unsaturated nitro compounds can be reduced to saturated amines by: Catalytic hydrogenation over palladium-on-carbon; Iron metal; Lithium aluminium hydride [27] (Note: Hydroxylamines and oximes are typical impurities.)
This can be economically viable if the products can be separated and both have a value; the commercial conversion of furfural into furfuryl alcohol and 2-furoic acid is an example of this. [6] Alternatively, higher yields of one product (usually the alcohol) can be achieved in the crossed Cannizzaro reaction , in which a sacrificial aldehyde is ...