Study on Synthesis of α-Acetonaphthone Oxime

Treatment of naphthalene with acetyl chloride in the presence of aluminum chloride by Friedel-Crafts reaction gave the intermediate α-acetonaphthone.Oximation reaction of α-acetonaphthone with hydroxylamine hydro-chloride afforded α-acetonaphthone oxime.The influences of AlCl3,reaction temperature and the addition method of acethyl chloride on Friedel-Crafts reaction and the influences of H2O,hydroxylamine hydro-chloride and base on oximation reaction were studied.The optimum conditions are as follows: the mole ratio of acetyl chloride to aluminum chloride is 1∶ 1.5,the reaction temperature is(25±2)℃,acetyl chloride is added at 0.3 mL/min in Friedel-Crafts reaction;the mole ratio of α-acetonaphthone,hydroxylamine hydro-chloride,water and sodium hydroxide is 1∶ 1.5～2.0∶ 4.30～34.0∶ 5.0 in oximation reaction.The total yield of α-acetonaphthone oxime is 87.0%.The improved experiment has many advantages such as the facilitated operation,easy isolation or purification of the product,and working safety,and instructional significance for industrial production and experimental teaching.