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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. Nucleophiles attack the carbonyl center, illustrated by hydrolysis with addition of aqueous NaOH to give methanol and sodium benzoate.
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-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 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.
Sodium hydrosulfite [10] Sodium sulfide (or hydrogen sulfide and base). Illustrated by the selective reduction of dinitrophenol to the nitroaminophenol. [11] Tin(II) chloride [12] Titanium(III) chloride; Samarium [13] Hydroiodic acid [14] Metal hydrides are typically not used to reduce aryl nitro compounds to anilines because they tend to ...
synthesis of benzamide from benzoyl chloride and a phenethylamine; synthesis of flutamide, a nonsteroidal antiandrogen; acylation of a benzylamine with acetyl chloride (acetic anhydride is an alternative) In the Fischer peptide synthesis (Emil Fischer, 1903), [6] an α-chloro acid chloride is condensed with the ester of an amino acid.
Mechanism of the benzoin addition. In this reaction, one aldehyde donates a proton and one aldehyde accepts a proton. Some aldehydes can only donate protons, such as 4-dimethylaminobenzaldehyde, whereas benzaldehyde is both a proton acceptor and donor. In this way it is possible to synthesise mixed benzoins, i.e. products with different groups ...
The most important esters with common protecting-group use are the acetate, benzoate, and pivalate esters, for these exhibit differential removal. Sterically hindered esters are less susceptible to nucleophilic attack: Chloroacetyl > acetyl > benzoyl > pivaloyl Trimethylsilyl chloride, activated with imidazole, protects a secondary alcohol