A novel method for quantitative analysis of acetylacetone and ethyl acetoacetate by fluorine-19 nuclear magnetic spectroscopy.

A new method utilization of NMR spectra was developed for structural and quantitative analysis of enol forms of acetylacetone and ethyl acetoacetate. Acetylacetone and ethyl acetoacetate were determined by (19) F NMR upon derivatisation with р-fluorobenzoyl chloride. The base-catalyzed derivatives of acetylacetone and ethyl acetoacetate reaction with р-fluorobenzoyl chloride were analyzed by (1) H and (13) C NMR spectroscopies. E and Z configurations of acetylacetone and ethyl acetoacetate were separated and purified by thin layer chromatography. In addition, the ability of (19) F NMR for quantitative analysis of acetylacetone by integration of the appropriate signals of the derivatives were tested and compared. The results further testified the enol forms of acetylacetone and ethyl acetoacetate and the feasibility of (19) F NMR method. This method can be potentially used to characterize E and Z isomers and quantitatively analyze E/Z ratio of β-diketone and β-ketoester homologues. Copyright © 2015 John Wiley & Sons, Ltd.