Ethyl benzoylacetate

Chemical properties

Brownish liquid

Chemical properties

Ethyl benzoylacetate has a brandy-like odor and sweet, woody, cherry, phenolic-like flavor.

The Uses of Ethyl benzoylacetate

Ethyl benzoylacetate (Best) is used as intermediate for different organic synthesis. Product Data Sheet

The Uses of Ethyl benzoylacetate

Ethyl benzoylacetate (Best) is used as an intermediate for different organic synthesis Product Data Sheet

The Uses of Ethyl benzoylacetate

Ethyl benzoylacetate (Benzoylacetic acid ethyl ester) was used to prepare ethyl 2-fluoro-2-benzolyacetate. It was also used to synthesize iodonium ylides.

Preparation

By condensation of ethyl benzoate with ethyl acetate (via Claisen condensation) using sodium ethoxide; another method also known.

Definition

ChEBI: Ethyl 3-oxo-3-phenylpropanoate is an aromatic ketone.

Taste threshold values

Taste characteristics at 10 ppm: sweet, cherry, fruity, berry-like with woody, jamy notes.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 28, p. 1864, 1985 DOI: 10.1021/jm00150a018
Journal of Heterocyclic Chemistry, 32, p. 723, 1995 DOI: 10.1002/jhet.5570320303
The Journal of Organic Chemistry, 38, p. 2731, 1973 DOI: 10.1021/jo00955a040

General Description

Ethyl benzoylacetate is an ester. It undergoes microbial reduction by bakers′ yeast (Saccharomyces cerevisiae), Beauveria sulfurescens or Geotrichum candidum to afford ethyl (S)-3-hydroxy-3-phenylpropionate. It undergoes Claisen condensation reaction with malononitrile to afford 2-cyano-5-phenyl-3,5-dioxopentanonitrile which on cyclization followed by coupling with diazonium salts yields azo derivatives.