Acetoxy group


Acetoxy group, abbreviated AcO or OAc, preferred IUPAC name acetyloxy, is a chemical functional group of the structure CH3-C-O-. It differs from the acetyl group CH3-C- by the presence of one 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 :
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