Isopropenyl Acetate
   HOME

TheInfoList



OR:

Isopropenyl acetate is an
organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
, which is the acetate ester of the enol tautomer of acetone. This colorless liquid is significant commercially as the principal precursor to
acetylacetone Acetylacetone is an organic compound with the chemical formula . It is classified as a 1,3-diketone. It exists in equilibrium with a tautomer . The mixture is a colorless liquid. These tautomers interconvert so rapidly under most conditions that ...
. In
organic synthesis Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...
, it is used to prepare enol acetates of ketones and
acetonide In organic chemistry, an acetonide is the functional group composed of the cyclic ketal of a diol with acetone. The more systematic name for this structure is an isopropylidene ketal. Acetonide is a common protecting group for 1,2- and 1,3-diols ...
s from
diol A diol is a chemical compound containing two hydroxyl groups ( groups). An aliphatic diol may also be called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting gro ...
s.


Preparation

Isopropenyl acetate is prepared by treating
acetone Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...
with
ketene In organic chemistry, a ketene is an organic compound of the form , where R and R' are two arbitrary valence (chemistry), monovalent functional group, chemical groups (or two separate Substituent, substitution sites in the same molecule). The na ...
. Upon heating over a metal surface, isopropenyl acetate rearranges to acetylacetone.


Reactions

Isopropenyl acetate is used to prepare other isopropenyl ethers. Isopropenyl acetate reacts with ketones to give new enol acetates: :{{chem2, CH2\dCH(OAc)CH3 + RC(O)CH3 -> CH2\dCH(OAc)R + (CH3)2C\dO


References

Acetate esters Isopropenyl esters