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Acetoxy group

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Acetoxy group

In organic chemistry, the acetoxy group (abbr. AcO– or –OAc; IUPAC name: acetyloxy), is a functional group with the formula −OCOCH3 and the structure −O−C(=O)−CH3. As the -oxy suffix implies, it differs from the acetyl group (−C(=O)−CH3) by the presence of an additional oxygen atom. The name acetoxy is the short form of acetyl-oxy.

An acetoxy group may be used as a protection for an alcohol functionality in a synthetic route although the protecting group itself is called an acetyl group.

There are several options of introducing an acetoxy functionality in a molecule from an alcohol (in effect protecting the alcohol by acetylation):

An alcohol is not a particularly strong nucleophile and, when present, more powerful nucleophiles like amines will react with the above-mentioned reagents in preference to the alcohol.

For deprotection (regeneration of the alcohol)

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