Reformatsky Reaction

Reformatsky Reaction

Reformatsky Reaction


Reformatsky Reaction

The reaction of α-halo ester with aldehydes or ketones in the presence of zinc metal to produce a β-hydroxy ester. This reaction is known as Reformatsky Reaction.
Reformatsky Reaction

Mechanism of Reformatsky Reaction

Reformatsky reaction usually commences with the oxidative addition or insertion of the zinc into the carbon-halogen bond of α-haloester. After the insertion, the compounds coordinate with each other leading to the formation of a dimer. This compound further experiences a rearrangement which results in the emergence of two zinc enolates. Then, the oxygen of the ketone or aldehyde coordinates to the zinc and a new rearrangement is formed where the two reagents now have a carbon-carbon bond between them. Following that, an acid workup splits the zinc and oxygen bond to generate zinc(II) salt and β-hydroxy ester as the final products.

Mechanism of Reformatsky Reaction

Applications of Reformatsky Reaction

Synthesis of α,β-unsaturated ester

Synthesis of alpha,beta-unsaturated ester

Synthesis of Citral

Synthesis of Citral

Synthesis of β-Phenylbutyric acid

Synthesis of beta-Phenylbutyric acid

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