Reformatsky reaction

What is Reformatsky reaction?

The Reformatsky reaction, or reformatskii reaction, is the condensation reaction to synthesize β-hydroxy esters by reacting an aldehyde or ketone with an α-halo ester in the presence of a zinc catalyst.

Reformatsky reaction
Reformatsky reaction

The reaction was developed by Victor Grignard and Henry Debré in the late 1800s and is named after Ivan Reformatsky, who first reported the reaction in 1887. It is an important method for the synthesis of β-hydroxy esters, which are widely used as precursors to a wide range of compounds and materials..

The reaction mechanism of the Reformatsky reaction involves the formation of a zinc enolate intermediate, which is formed by the deprotonation of the aldehyde or ketone by the zinc catalyst. The intermediate then reacts with the α-halo ester to form the β-hydroxy ester product..

One of the main advantages of the Reformatsky reaction is its compatibility with a wide range of functional groups, including alkyl, aryl, and vinyl groups. This makes it a useful method for synthesizing a wide range of β-hydroxy esters and other compounds..

The Reformatsky reaction is typically performed under mild reaction conditions, which makes it suitable for synthesizing sensitive and labile compounds. However, it can be prone to side reactions, such as the formation of unwanted byproducts, which can reduce the yield and selectivity of the reaction..

There are several variations of the Reformatsky reaction that have been developed to improve its efficiency and scope, including the use of different catalysts and the use of modified reaction conditions. For example, the use of a lithium or magnesium base as a catalyst has been shown to improve the yield and selectivity of the Reformatsky reaction..

Summary

Reformatsky reaction is a powerful tool for synthesizing β-hydroxy esters and has numerous applications in the chemical and pharmaceutical industries. It is an important method in organic chemistry and continues to be an area of active research and development..

References

  • Reformatsky, S. (1887), Neue Synthese zweiatomiger einbasischer Säuren aus den Ketonen. [New synthesis of diatomic monobasic acids from the ketones.] Ber. Dtsch. Chem. Ges., 20: 1210-1211. https://doi.org/10.1002/cber.188702001268
  • S. Reformatskii, J. Russ. Phys. Chem. Soc. 22, 44 (1890)
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