6-氯-5-羟基-1,4-萘醌的全合成及其染色性能研究

摘要

In this paper,a method for the synthesis of 6-chloro-5-hydroxyl-1,4-naphthoquinone (6) was presented using glycerol (1) as material and through 1,2-dihydroxyl protection,Oppenheimer oxidation,Darzens condensation,rearrangement-cyclization reaction to construct the skeleton of 4-chloro-3-hydroxy-2-pyrone (5),followed by Diels-Alder reaction and decarboxylation-oxidation.Under the condition of free-solvent,the yield of (2,2-dimethyl-1,3-dioxolan-4-yl) methanol (2),2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (3) or 2-chloro-3-(2,2-dimethyl-1,3-dioxolan-4-yl)oxirane2-car-boxy-late (4) is over 99.3 %,73.4 % or 98.0 %,respectively.The ultimate yield of target compound 6 is over 64.6 % after five steps synthesis.Furthermore,based on the sulfonation of Compound 6,the influences of concentration,pH value,temperature and time on dyeing properties of wool fabric were investigated,and environment-friendly mordant such as Fe2+,Fe3+ or Al3+ was adapted.It was concluded that sulfonated Compound 6 had superior chromaticity and fastnesses by mordant dyeing with Fe3+u0000per%本文提供了一种以甘油(1)为原料的6-氯-5-羟基-1,4-萘醌(6)的全合成方法,即先通过1,2-二羟基保护、氧化、缩合及重排反应构建4-氯-3-羟基-2-吡喃酮(5)的骨架,再通过Diels-Alder和脱羧氧化反应得到目标产物.在无溶剂条件下,2,2-二甲基-1,3-二氧戊环-4-甲醇(2)、2,2-二甲基-1,3-二氧戊环-4-甲醛(3)以及2-氯-3-(2,2-二甲基-1,3-二氧戊环-4-基)氧丙环-2-羧酸酯(4)的产率分别超过99.3％、73.4％或98.0％.五步合成之后,目标化合物6的产率超过了64.6％；在将化合物6进行磺化的基础上,探讨了浓度、pH值、温度及时间对毛织物染色性能的影响,并采用环境友好型媒染剂Fe2+、Fe3+和Al3+等进行媒染.研究表明,通过Fe3+的媒染作用,化合物6的磺化产物对毛织物有着良好的色度参数和摩擦牢度.