Synthesis And Characterization Of The Ester Derivatives. Aryl ¦Ã-keto Esters Of ¦Ã-butyrolactone

A series of aryl y-Keto esters were synthesized using ethyl succinyl chloride (ESC) and aromatic compounds such as anisole, toluene, tert-butylbenzene, benzene, bromobenzene by the Friedel-Crafts acylation reaction. Hydrolyze aryl y-Keto esters with NaO/C2H5OH to give aryl y-Keto acid. Aryl y-lactones were prepared from aryl y-Keto acids, benzaldehyde or anisaldehyde by condensation reaction, rearrangement, esterification. The products were characterized by spectrum of IR,1H-NMR, MS.Effect of the reactants ratio, reaction temperature, reaction time and solvent on the reaction was investigated through single variable experiments. The optimum reaction conditions were obtained. The yield of aryl y-Keto esters was 49%～80% when the mole ratio of ethyl succinyl chloride and aromatic compounds was 1.5:1, reaction temperature was 20℃, reaction time was 15h. The regioselectivity of the reaction was studied by high performance liquid chromatography. The yield of arylγ-Keto acid was 94% when the mass ratio of NaOH/ C2H5OH and arylγ-Keto esters was 3.5:1, reaction temperature was 70℃, reaction time was 2h. By using the solvent of 1,4-dioxane, the yield of Aryl y-lactone was 49% when the mole ratio of benzaldehyde and aryl y-Keto acid was 1.5:1, reaction temperature was 95℃, reaction time was 2h.