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摘要：8-羟基-8-(2-呋喃)辛酸甲酯属于呋喃类化合物，呋喃类化合物主要是一类化学合成药，具有许多潜在的医学价值。本实验以辛二酸单甲酯和乙酰氯为原料，以四氯化碳为溶剂，三乙胺为缚酸剂，室温下搅拌3h，得到相应的酸酐，然后过滤除去反应生成的盐，在滤液中加入呋喃，三氟化硼乙醚溶液作催化剂，搅拌12h，得到8-（2-呋喃）-8-辛酮酸甲酯，经硼氢化钾还原得到8-羟基-8-(2-呋喃)辛酸甲酯。本实验主要讨论乙酰氯与辛二酸单甲酯反应时间，乙酰氯的用量、呋喃的用量及硼氢化钾用量对实验结果的影响。从而确定8-（2-呋喃）-8-辛酮酸甲酯的最佳工艺合成条件为：辛二酸单甲酯与乙酰氯最佳配比为1:1.1；反应时间3h；辛二酸单甲酯与呋喃最佳配比为1:1.5；反应时间为12h，产率为88％。8-羟基-8-(2-呋喃)辛酸甲酯的最佳工艺条件：8-（2-呋喃）-8-辛酮酸甲酯与硼氢化钾的最佳比例为1:1.1，产率为80%。产物结构经1HNMR进行表征。41082
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毕业论文关键词：辛二酸单甲酯；8-（2-呋喃）-8-辛酮酸甲酯；8-羟基-8-(2-呋喃)辛酸甲酯；呋喃；合成
Synthesis of methyl8-(furan-2-yl)-8-hydroxyoctanoate
Abstract: 8-hydroxy-8- (2-furan) octanoate belonging to furan compounds, furan compounds are a major class of chemical synthetic drugs, has many potential medical value. In this experiment, suberic acid monomethyl ester and acetyl chloride as raw materials, carbon tetrachloride as a solvent, triethylamine as acid binding agent, at room temperature for 3h, to give the corresponding acid anhydride, and then filtered to remove the salt produced by the reaction, in furanfiltrate was added boron trifluoride etherate as the catalyst solution was stirred 12h, to give 8- (2-furyl) -8-methyl octyl ketone, by potassium borohydride reduction to give 8-hydroxy-8- (2-furyl ) octanoate. This experiment focuses chloride with suberic acid monomethyl ester reaction time, the amount of acetyl chloride, furan affect the amount of potassium borohydride and the amount of experimental results. Thereby determining 8- (2-furan) -8 optimum synthesis conditions Octanone methyl is: suberic acid monomethyl ester chloride and the best ratio of 1: 1.1; the reaction time 3h; suberate mono-methyl furan and the best ratio of 1: 1.5; the reaction time was 12h, 88% yield. 8- hydroxy-8-optimal conditions (2-furyl) methyl caprylate: 8- (2-furyl) -8-methyl ketone and the best ratio oct potassium borohydride is 1: 1.1, yield 80%. The product structure was characterized by 1HNMR.
Keywords: 8- (2-furan) -8-methyl pyruvate;8-hydroxy-8- (2-furan) octanoate; furan; suberic acid monomethyl ester synthesis
目录
1 前言 1
1.1 开题依据 1
1.1.1 呋喃类的化合物在药物方面的用途 1
1.1.2 呋喃类物质在香料方面的应用 2
1.1.3 呋喃类物质在材料方面的应用 3
1.1.4 呋喃类物质在燃料方面的应用 4
1.2 文献综述 4
1.2.1芳羟基酸酯的合成反应 4
1.2.2 羰基化合物的还原 7
1.3 合成路线 8
1.4 研究内容 8
1.5 方案论证 8
2 实验部分 10
2.1 仪器与试剂 10
2.1.1 仪器 10
2.1.2 试剂 10
2.2 实验步骤 11
2.2.1 2-呋喃乙酮的制备 11
2.2.2 显色剂的制备 11
2.2.3 8-（2-呋喃）-8-辛酮酸甲酯的制备 11
2.2.4 8-羟基-8-(2-呋喃)辛酸甲酯的制备 12
3 结果与讨论 13
3.1 目标产物的合成 13
3.1.1 制备酸酐的原料的选择对8-（2-呋喃）-8-辛酮酸甲酯的影响 13