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The archetypal Beckmann rearrangement [4] is the conversion of cyclohexanone to caprolactam via the oxime. Caprolactam is the feedstock in the production of Nylon 6. [5] The Beckmann solution consists of acetic acid, hydrochloric acid and acetic anhydride, and was widely used to catalyze the rearrangement.
Cyclohexanone is the organic compound with the formula (CH 2) 5 CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group . This colorless oily liquid [ 3 ] has a sweet odor reminiscent of benzaldehyde .
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 ]
It can be obtained from cyclohexanone by α-bromination followed by treatment with base. Hydrolysis of 3-chloro cyclohexene followed by oxidation of the cyclohexenol is yet another route. Cyclohexenone is produced industrially by catalytic oxidation of cyclohexene, for example with hydrogen peroxide and vanadium catalysts.
The Stork enamine alkylation involves the addition of an enamine to a Michael acceptor (e.g., an α,β -unsaturated carbonyl compound) or another electrophilic alkylation reagent to give an alkylated iminium product, which is hydrolyzed by dilute aqueous acid to give the alkylated ketone or aldehyde. [1]
Upon heating in cyclohexanone, amino acids decarboxylate. In the related Hammick reaction, uncatalyzed decarboxylation of a picolinic acid gives a stable carbene that attacks a carbonyl electrophile. Oxidative decarboxylations are generally radical reactions. These include the Kolbe electrolysis and Hunsdiecker-Kochi reactions.
Caprolactone is prepared industrially by Baeyer-Villiger oxidation of cyclohexanone with peracetic acid. Caprolactone is a monomer used in the production of highly specialised polymers. Ring-opening polymerization, for example, gives polycaprolactone. [3] Another polymer is polyglecaprone, used as suture material in surgery. [4]
Basic hydrolysis to remove the hydroxyl ester moiety of pleuromutilin yielded mutilin. Subsequent treatment with lithium hexamethyldisilazide (LiHMDS) and TMSCl gave the TMS-protected silyl enol ether, which was immediately subjected to an acetic acid - (HOAc) pyridine - (Py) buffered Rubottom oxidation before acidic hydrolysis to afford 2S ...