What is uses and synthesis of Phenyl acetate?

Phenyl acetate is the ester of phenol and acetic acid. It can be produced by reacting phenol with acetic anhydride or acetyl chloride.

Reactions

Phenyl acetate can be separated into phenol and an acetate salt, via saponification: heating the phenyl acetate with a strong base, such as sodium hydroxide, will produce phenol and an acetate salt (sodium acetate, if sodium hydroxide were used).

Uses

Phenyl acetate is mainly used as a solvent and an intermediate in organic synthesis. Phenyl acetate can also be converted into hydroxyacetophenone through a transposition reaction, which is used to treat acute and chronic icteric hepatitis, cholecystitis and other diseases.

Synthesis

As seen on the reaction scheme above, this process involves the exchange of the alkyl group of the previously existing ester. That way, the corresponding ester of the alcohol starting material is formed. This synthesis is usually facilitated by the presence of an acidic or basic catalyst. In this synthesis, a N-heterocyclic carbene was used as the catalyst. ^[1]

According to literature, transesterification is preferable compared to the conventional esteri fication from carboxylic acid and alcohol since some carboxylic acids are less soluble in organic solvents and will thus seldom undergo a homogeneous esterification. Due to them often being commercially available, mostly methyl- and ethyl esters are used in transesterification reactions. Transesterification is widely applied not for laboratory synthetic purposes only but in various industrial processes, for example: 1. Polymerisation (e.g. polyester production). 2. Biodiesel production from oil seeds, vegetable oils, animal fats, waste cooking oil and microbial lipids. 3. In food processing.   The transesterification reaction encourages sustainability, since the process principles atom economy and waste reduction at source.

Reference

[1] Otera, J., Chem. Rev. 1993, 93, 1449-1470.

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