CN114956968A - 一种羰基化合物的制备方法 - Google Patents
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Abstract
本发明公开了一种羰基化合物的制备方法。该方法的原料为羟基位于α位的苯基醇,溶剂为1,2‑二氯乙烷或其与水的混合溶液;其具体过程包括:当羟基不位于烃链末端时,将原料加入溶剂中,在波长为365nm的光源下照射,直至原料完全转化,得到羰基化合物;当羟基位于烃链末端时,则在上述过程中加入碘化钠和硫代硫酸钠进行反应。本发明的方法可在室温和空气条件下进行,绿色环保、无需添加任何光催化剂、底物普适性强、原子利用高、反应选择性高、后处理简便、实验成本低,有利于规模化应用。
Description
技术领域
本发明属于羰基化合物的合成领域,具体涉及一种羰基化合物的制备方法。
背景技术
醛/酮化合物是一类极其重要的大宗化工品,常作为有机合成中间体,广泛用于药物分子、功能材料和天然产物的制备等领域,如何高效地构建这一砌块是合成化学的研究热点问题之一。醇脱氢反应具有原子利用率高、反应选择性高等优点,被认为是具有重要应用价值的制备羰基化合物的有机反应。
当前,实现醇脱氢反应主要有热化学和光化学方法两种。其中,热化学方法需要等当量的强氧化剂(例如:KMnO4、CrO3等)甚至高温,这不仅限制了该方法的底物兼容性,而且产生的反应废液污染环境,不利于该方法的规模化应用。
光化学方法作为一种绿色合成技术,广泛用于诱导醇脱氢反应,制备醛/酮化合物。但这些方法仍依赖于各种光催化剂,例如共轭聚合物、金属配合物、无机半导体材料等,使得醛/酮化合物的制备需要额外的步骤合成光催化剂,且催化剂的重复催化性能差,增加了能源消耗和实验成本,不利于方法的产业化。
发明内容
本发明的目的是解决现有技术的不足,提供一种无需催化剂参与的绿色制备醛/酮化合物的光化学合成技术,具体采用以下的技术方案:
一种羰基化合物的制备方法,原料为羟基位于α位的苯基醇,溶剂为1,2-二氯乙烷或其与水的混合溶液;
当所述原料的羟基不位于烃链的末端时,具体步骤为步骤a,其具体过程为:将所述原料加入溶剂中,在波长为365nm的光源下照射,直至所述原料完全转化,得到所述羰基化合物;
当所述原料的羟基位于烃链的末端时,具体步骤为步骤b,其具体过程为:将所述原料加入溶剂中,同时加入碘化钠和硫代硫酸钠,在波长为365nm的光源下照射,直至所述原料完全转化,得到所述羰基化合物。
本申请中的羰基化合物为醛或酮。
优选地,在上述步骤中,当所述原料完全转化后,采用二氯甲烷或乙酸乙酯进行萃取,然后干燥、过滤、浓缩;随后柱层析分离得到醛基化合物或者热乙醇重结晶得到酮基化合物。其中,优选采用体积比为1:30的乙酸乙酯和石油醚的混合溶液作为流动相进行柱层析。
优选地,在上述步骤中,所述原料与1,2-二氯乙烷的比例为10mmol:5mL,所述原料、1,2-二氯乙烷和水的比例为10mmol:5mL:1mL,所述原料、碘化钠和硫代硫酸钠的比例为10mmol:30mmol:10mmol。所述原料为二苯甲醇、1-苯乙醇或4-氯苯甲醇。
本发明的有益效果为:本发明的方法可在室温和空气条件下进行,绿色环保、无需添加任何光催化剂、底物普适性强、原子利用高、反应选择性高、后处理简便、实验成本低,有利于规模化应用。
附图说明
图1所示为二苯甲酮的核磁氢谱图;
图2所示为二苯甲酮的碳谱图;
图3所示为苯甲酮的核磁氢谱图;
图4所示为苯甲酮的碳谱图;
图5所示为4-氯苯甲醛的核磁氢谱图;
图6所示为4-氯苯甲醛的碳谱图。
具体实施方式
以下将结合实施例和附图对本发明的构思及产生的技术效果进行清楚、完整的描述,以充分地理解本发明的目的、方案和效果。
实施例1:
称取二苯甲醇(1.84g,10mmol)溶于5mL 1,2-二氯乙烷中,反应体系在空气和室温条件下采用365nm(45W)光源照射5小时后,反应底物完全转化,浓缩除去有机溶剂,所得粗产品采用热乙醇重结晶,得到二苯甲酮产物(分离产率:97%)。其核磁氢谱图如图1所示,其碳谱图如图2所示。
实施例2:
称取1-苯乙醇(1.22g,10mmol)溶于5mL 1,2-二氯乙烷中,反应体系在空气和室温条件下采用365nm(45W)光源照射20小时后,反应底物完全转化;浓缩除去有机溶剂,所得粗产品采用乙酸乙酯和正己烷重结晶,得到苯甲酮产物(分离产率:95%)。其核磁氢谱图如图3所示,其碳谱图如图4所示。
实施例3:
称取4-氯苯甲醇(1.42g,10mmol)溶于5mL 1,2-二氯乙烷和1mL蒸馏水中,同时加入30mmol碘化钠和10mmol硫代硫酸钠作为助剂,所得反应体系在空气和室温条件下采用365nm光源照射5小时后,反应底物完全转化;反应完成后,萃取,浓缩,采用乙酸乙酯和石油醚(v:v=1:30)为流动相柱层析,得到4-氯苯甲醛(分离产率:92%)。其核磁氢谱图如图5所示,其碳谱图如图6所示。
对比例1:
称取二苯甲醇(1.84g,10mmol)溶于5mL 1,2-二氯乙烷中,反应体系在空气和室温条件下采用420nm(45W/180W)光源照射120/72小时后,反应底物转化完全,浓缩除去有机溶剂,所得粗产品采用热乙醇重结晶,得到二苯甲酮产物(分离产率:96%)。
对比例2:
称取4-氯苯甲醇(1.42g,10mmol)溶于5mL四氢呋喃和1mL蒸馏水中,同时加入30mmol碘化钠和10mmol硫代硫酸钠作为助剂,所得反应体系在空气和室温条件下采用365nm光源照射27小时后,反应底物完全转化;反应完成后,萃取,浓缩,采用乙酸乙酯和石油醚(v:v=1:30)为流动相柱层析,得到4-氯苯甲醛(分离产率:64%)。
由实施例1-3和对比例1-2的结果可知,本发明限定的波长和溶剂对于产率和反应时间有着巨大的影响,这是现有文献中未有报道过的,现有文献基本还是按照背景技术中采用添加光催化剂的手段进行反应。
以上所述,只是本发明的较佳实施例而已,本发明并不局限于上述实施方式,只要其以相同的手段达到本发明的技术效果,都应属于本发明的保护范围。在本发明的保护范围内其技术方案和/或实施方式可以有各种不同的修改和变化。
Claims (5)
1.一种羰基化合物的制备方法,其特征在于,原料为羟基位于α位的苯基醇,溶剂为1,2-二氯乙烷或其与水的混合溶液;
当所述原料的羟基不位于烃链的末端时,具体步骤为步骤a,其具体过程为:将所述原料加入溶剂中,在波长为365nm的光源下照射,直至所述原料完全转化,得到所述羰基化合物;
当所述原料的羟基位于烃链的末端时,具体步骤为步骤b,其具体过程为:将所述原料加入溶剂中,同时加入碘化钠和硫代硫酸钠,在波长为365nm的光源下照射,直至所述原料完全转化,得到所述羰基化合物。
2.根据权利要求1所述的制备方法,其特征在于,当所述原料完全转化后,采用二氯甲烷或乙酸乙酯进行萃取,然后干燥、过滤、浓缩;随后柱层析分离得到醛基化合物或者热乙醇重结晶得到酮基化合物。
3.根据权利要求2所述的制备方法,其特征在于,采用体积比为1:30的乙酸乙酯和石油醚的混合溶液作为流动相进行柱层析。
4.根据权利要求1所述的制备方法,其特征在于,所述原料与1,2-二氯乙烷的比例为10mmol:5mL,所述原料、1,2-二氯乙烷和水的比例为10mmol:5mL:1mL,所述原料、碘化钠和硫代硫酸钠的比例为10mmol:30mmol:10mmol。
5.根据权利要求1所述的制备方法,其特征在于,所述原料为二苯甲醇、1-苯乙醇或4-氯苯甲醇。
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