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The structure of the acetoxy group   blue.

In organic chemistry, the acetoxy group (abbr. AcO or OAc; IUPAC name: acetyloxy[1]), 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.

Functionality

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.

Alcohol protection

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.

Alcohol deprotection

For deprotection (regeneration of the alcohol)

See also

References

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 805. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4. The systematic name 'acetyloxy' is preferred to the contracted name 'acetoxy' that may be used in general nomenclature.
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