Reformatsky reaction

The Reformatsky reaction is a name reaction in organic chemistry, which was named after its discoverer Sergei Reformatski. The reaction is used for the synthesis of β - hydroxy esters. This is one of a α - halogenated carboxylic acid esters with zinc dust and an aldehyde or ketone.

Overview reaction

A ketone or aldehyde (or if R1 = H or R2 = H) is reacted with an α - halogenated carboxylic acid ester, which has been previously reacted with metallic zinc. The organozinc compound is then hydrolyzed to a β - hydroxycarboxylic. The Reformatsky reaction is similar to the Grignard reaction.

Mechanism

The Reformatsky reagent, an organozinc compound similar to the Grignard reagent, obtained from an α - halogenated carboxylic acid esters, and zinc dust.

It then reacts with the carbonyl then added a ketone or aldehyde. The nucleophilic Reformatsky reagent adds to the carbonyl and forms an alkoxide, which yields aqueous workup the desired β - hydroxy carboxylic acid ester.

In contrast to the reactive Grignard reagents react in the Reformatsky reaction, only ketones and aldehydes, but not ester carbonyl.