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黄烷酮的合成以往多采用查尔酮的关环或邻羟基苯乙酮与芳香醛的直接缩合关环,近年来,人们主要在关环上做了些改进,但因此类化合物多带羟基,在强酸、强碱中易发生副反应,所以一般须将羟基预先进行保护才能得到较满意的结果,本文采用芳香醛、丙二腈为原料,在乙酸铵和乙酸的催化作用下,先进行Knoevenagel羟醛缩合,得到苯甲叉丙二腈1,然后1与间苯三酚在无水ZnCl_2和HCl气体的催化作用下,进行Hoesch单酰基化反应,保留的一个氰基水解成羧基,因是β-酮酸结构,故易脱羧,同时关环,顺利得到黄烷酮2,收率≥60%,可能的反应历程如下式所示:
The synthesis of flavanone in the past often use chalcone ring or o-hydroxyacetophenone and aromatic aldehydes direct condensation ring, in recent years, people have done some improvements in the ring, but the class compound with hydroxyl , In the strong acid, alkali prone to side reactions, it is generally required to be pre-protected hydroxyl to get more satisfactory results, this paper uses aromatic aldehydes, malononitrile as raw materials, ammonium acetate and acetic acid catalysis, the first Knoevenagel aldol condensation to give benzylidenedadiponitrile 1, then 1 and phloroglucinol in the presence of anhydrous ZnCl 2 and HCl gas catalytic Hoesch monoacylation reaction, the retention of a cyano group is hydrolyzed into a carboxyl group due to Is β-keto acid structure, it is easy to decarboxylation, at the same time turn off the ring, smoothly flavanone 2, the yield ≥ 60%, the possible reaction process is shown below: