Benzoylacetonitrile

At room temperature, a solution of KOt pentanol (1.33 mL, 2.61 mmol, 3.00 equivalence, 1.7 mol, toluene, Fluka) was added dropwise to a stirred solution of acetonitrile (0.87 mmol, 1.00 equivalence) in THF (3.0 mL), followed by the addition of the ester (3.48 mmol, 4.00 equivalence). After 20 minutes at room temperature, the reaction mixture was diluted with HCl (0.25 mL, 100 mL) and EtOAc (100 mL). The layers were separated and the organic layer was washed sequentially. Finally, the mixture was dried over Na2SO4 with H2O (2 x 50 mL) and brine (2 x 50 mL), filtered, concentrated, and chromatographically analyzed (silica gel, EtOAc/Hex) to provide the corresponding benzoylacetonitrile.

Figure: Structural formula of benzoylacetonitrile

LIGHT YELLOW TO YELLOW-BROWN CRYSTALLINE POWDER

Benzoylacetonitrile is used to produce 2-benzoyl-3-furan-2-yl-acrylonitrile. It is also used in the synthesis of substituted naphtho[1,8-bc]pyrans and as building block in the preparation of 4H-pyrans, 2-pyridones, furans and carbocyclics. It is an active methylene compound, useful in heterocyclic synthesis, e.g. polyfunctional pyridines and pyrimidines.

Benzoylacetonitrile can be used as a building block for the preparation of 4H-pyrans, 2-pyridones, furans and carbocyclics

ChEBI: Benzoylacetonitrile is a beta-ketonitrile and an aromatic ketone. It is functionally related to a benzoic acid.

The Journal of Organic Chemistry, 54, p. 4229, 1989 DOI: 10.1021/jo00278a047
Synthesis, p. 308, 1983
Tetrahedron, 49, p. 5091, 1993 DOI: 10.1016/S0040-4020(01)81874-3