benzilate

Benzilate is a chemical term used to denote the salts or esters derived from benzilic acid. Benzilic acid itself is an alpha-hydroxy carboxylic acid produced by the benzil–benzilic acid rearrangement and has the structure Ph2C(OH)CO2H, where Ph denotes a phenyl group. The benzilate designation commonly refers to the benzilitic anion formed by deprotonation of the carboxyl group, [C14H11O3]−, as well as to the corresponding inorganic salts such as sodium benzilate and potassium benzilate. It also encompasses esters in which the carboxyl hydrogen is replaced by an alkyl group (for example methyl benzilate).

Preparation and properties

Benzilate salts can be prepared by neutralizing benzilic acid with a base (e.g., NaOH or KOH). Esterification of benzilic acid with alcohols under acidic catalysis yields alkyl benzilates. The benzilate anion is stabilized by resonance and is typically soluble in polar solvents; the accompanying cation in salts influences solubility and crystallinity.

Uses

Benzilates are primarily encountered as intermediates in organic synthesis. They can serve as sources of the benzil fragment in a range of transformations and may function as ligands or building blocks in synthetic chemistry. They are more commonly encountered in laboratory and academic contexts than in large-scale industrial production.

Safety and handling

As with many carboxylate reagents, benzilates should be handled with standard laboratory precautions. Avoid ingestion, inhalation of dust or solutions, and contact with skin or eyes. Refer to material safety data sheets for specific salts or esters.