Orthoester

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The chemical structure of ethyl orthoacetate, an orthoester.
The chemical structure of ethyl orthoacetate, an orthoester.

In organic chemistry, an orthoester is a functional group containing three alkoxy groups attached to one carbon atom. The name can also refer to any organic compound that contains this functional group. An example of an orthoester is ethyl orthoacetate, CH3C(OCH2CH3)3. Othoesters are used in organic synthesis as protecting groups for esters.

Othoesters can be prepared by the reaction of nitriles with alcohols under acid catalysis:

RCN + 3 R’OH → RC(OR’) 3 + NH3

Othoesters are readily hydrolyzed in mild aqueous acid to form esters:

RC(OR’) 3 + H2O → RCO2R’ + 2 R’OH
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