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The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction which involves the base-induced disproportionation of two molecules of a non-enolizable aldehyde to give a primary alcohol and a carboxylic acid. [1] [2]
In the Cannizzaro reaction, formaldehyde and base react to produce formic acid and methanol, a disproportionation reaction. Hydroxymethylation and chloromethylation
Neopentyl glycol is synthesized industrially by the aldol reaction of formaldehyde and isobutyraldehyde.This creates the intermediate hydroxypivaldehyde, which can be converted to neopentyl glycol by either a Cannizzaro reaction with excess formaldehyde, or by hydrogenation using palladium on carbon.
The reaction exhibits an induction period, during which only the nonproductive Cannizzaro disproportionation of formaldehyde (to methanol and formate) occurs. The initial dimerization of formaldehyde to give glycolaldehyde ( 1 ) occurs via an unknown mechanism, possibly promoted by light or through a free radical process and is very slow.
Pentaerythritol was first reported in 1891 by German chemist Bernhard Tollens and his student P. Wigand. [5] It may be prepared via a base-catalyzed multiple-addition reaction between acetaldehyde and 3 equivalents of formaldehyde to give pentaerythrose (CAS: 3818-32-4), followed by a Cannizzaro reaction with a fourth equivalent of formaldehyde to give the final product plus formate ion.
It undergoes the Cannizzaro reaction even though it has alpha hydrogen atom. It is a colorless volatile liquid. ... Condensation with formaldehyde gives ...
Trimethylolethane is produced via a two step process, starting with the condensation reaction of propionaldehyde with formaldehyde: CH 3 CH 2 CHO + 2 CH 2 O → CH 3 C(CH 2 OH) 2 CHO. The second step entails a Cannizzaro reaction: CH 3 C(CH 2 OH) 2 CHO + CH 2 O + NaOH → CH 3 C(CH 2 OH) 3 + NaO 2 CH. A few thousand tons are produced annually ...
For laboratory use, Grignard reaction of phenylmagnesium bromide (C 6 H 5 MgBr) with formaldehyde and the Cannizzaro reaction of benzaldehyde also give benzyl alcohol. The latter also gives benzoic acid, an example of an organic disproportionation reaction.