Synthesis of Some Acetophenone Oximes and Their Corresponding Bridged Terphthaloyl Oxime Esters

The objective of this study is to synthesize a number of oximes along with their terphthaloyl oxime esters derived from acetophenone, 4-methylacetophenone, 4-hydroxyacetophenone, 4-aminoacetophenone and 4-nitroacetophenone as a part of ongoing research. Five acetophenone oximes have been synthesized by refluxing the acetophenone derivative with a solution of hydroxylamine hydrochloride in the presence of potassium hydroxide. The corresponding acetophenone oximes were obtained as solid materials in moderate to good yields. The structures of the resulting oximes were confirmed using IR, NMR and mass spectrometer. The HNMR data revealed that one oxime of the synthesized oximes was obtained as a mixture of two E/Z isomers in a ratio of (8:1). These resulting oximes were subjected into an esterification process with the terphthaloyl chloride in molar ratio of (1:2) respectively. The esterification reaction was carried out under basic conditions at 0 – 5 ºC then room temperature. The five corresponding bridged terphthaloyl oxime esters have been formed as solid materials in moderate yields. The structures of the obtained terphthaloyl esters were also confirmed by spectroscopic techniques such as IR, NMR and mass spec.