2-羟基-5-特辛基苯乙酮肟的合成及表征

Synthesis and characterization of 2-hydroxy-5-octyl phenyl ethyl ketoxime

以四氯乙烯为溶剂,对特辛基苯酚、乙酰氯、无水AlCl3和盐酸羟胺为主要原料,采用分步合成法合成了2-羟基-5-特辛基苯乙酮肟.考察了无水AlCl3用量、乙酰氯的用量、Fries重排温度、肟化反应盐酸羟胺用量以及缚酸剂无水碳酸钠用量对产物产率的影响,实验结果表明,当n(AlCl3)∶n(乙酰氯)∶n(对特辛基苯酚)=1.5∶2∶1,Fries重排温度为120℃,n(Na2CO3)∶n(盐酸羟胺)∶n(对特辛基苯酚)=0.5∶1∶1.产物收率64.9%.对合成产物利用核磁共振进行了结构表征.

2-hydroxy-5-octyl phenyl ethyl ketoxime is prepared by three-step method using tetrachloroethylene as solvent, p-（tert-octyl）phenol, acetyl chloride, anhydrous aluminum chloride and hydroxylamine hydrochloride as raw materials. The effects of anhydrous aluminum chloride dosage, acetyl chloride dosage, Fries rearranging temperature, dosages of hydroxylamine hydrochloride and acid-binding agent anhydrous sodium carbonate in oximation reaction on the yield of 2-hydroxy-5-octyl phenyl ethyl ketoxime are investigated. The results show that the reaction rate of 2-hydroxy-5-octyl phenyl ethyl ketoxime production yield reaches 64.9 % under optimum reaction conditions： the mole ratio of anhydrous aluminum chloride, acetyl chloride and p-（tert-octyl）phenol is 1.5：2：1. Fries rearranging temperature is 120 ℃ and the mole ratio of anhydrous sodium carbonate,acetyl chloride and p-（tert-octyl）phenol is 0.5：1：1. The molecular structure of the product is characterized with nuclear magnetism resonance spectrum.