orthoesterification

Orthoesterification is a chemical reaction used to synthesize orthoesters. Orthoesters are organic compounds with the general formula RC(OR')3. They are also known as orthoalkyl esters or trialkyl orthoesters.

The most common method for orthoesterification involves the reaction of a nitrile with an alcohol in the presence of an acid catalyst. For example, the reaction of acetonitrile with ethanol in the presence of a strong acid like sulfuric acid yields ethyl orthoacetate. Alternatively, orthoesters can be formed by the reaction of an ester with an alcohol in the presence of an acid catalyst and a dehydrating agent. Another method involves the reaction of an aldehyde or ketone with an orthoformate ester, often under acidic conditions.

Orthoesters are useful intermediates in organic synthesis. They can be hydrolyzed to esters, transesterified with other alcohols, or used in various condensation reactions. For instance, they are employed in the synthesis of heterocyclic compounds and as protecting groups for carboxylic acids. The Pinner reaction is a notable orthoesterification process used to prepare imino ethers, which can then be further reacted to form orthoesters. The reaction conditions and choice of catalyst are crucial for the successful formation of orthoesters and to avoid side reactions, such as the formation of normal esters.