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Benzaldehyde oxime undergoes Beckmann rearrangement to form benzamide, catalyzed by nickel salts [3] or photocatalyzed by BODIPY. [4] Its dehydration yields benzonitrile. It can be hydrolyzed to regenerate benzaldehyde. [5]
Examples: synthesis of N-vanillyl nonanamide, also known as synthetic capsaicin; 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)
Benzoic acid (/ b ɛ n ˈ z oʊ. ɪ k /) is a white (or colorless) solid organic compound with the formula C 6 H 5 COOH, whose structure consists of a benzene ring (C 6 H 6) with a carboxyl (−C(=O)OH) substituent.
Benzamide is an organic compound with the chemical formula of C 7 H 7 NO. It is the simplest amide derivative of benzoic acid. In powdered form, it appears as a white solid, while in crystalline form, it appears as colourless crystals. [5] It is slightly soluble in water, [2] and soluble in many organic solvents. [6]
The Hinsberg reaction is a chemical test for the detection of primary, secondary and tertiary amines.The reaction was first described by Oscar Hinsberg in 1890. [1] [2] In this test, the amine is shaken well with the Hinsberg reagent (benzenesulfonyl chloride) in the presence of aqueous alkali (either KOH or NaOH).
An example is shown below. [9] Scheme 2. An intramolecular benzoin addition. Since the products of the reaction are thermodynamically controlled, the retro benzoin addition can be synthetically useful. If a benzoin or acyloin can be synthesized by another method, then they can be converted into the component ketones using cyanide or thiazolium ...
Acid–base-catalysed hydrolyses are very common; one example is the hydrolysis of amides or esters. Their hydrolysis occurs when the nucleophile (a nucleus-seeking agent, e.g., water or hydroxyl ion) attacks the carbon of the carbonyl group of the ester or amide. In an aqueous base, hydroxyl ions are better nucleophiles than polar molecules ...
The hydrolysis of oximes proceeds easily by heating in the presence of various inorganic acids, and the oximes decompose into the corresponding ketones or aldehydes, and hydroxylamines. The reduction of oximes by sodium metal, [ 10 ] sodium amalgam , hydrogenation , or reaction with hydride reagents produces amines . [ 11 ]