CN111484397A - (2-羟基苯基)(2,4,6-三甲氧基苯基)(苯基)甲烷及其合成方法 - Google Patents
(2-羟基苯基)(2,4,6-三甲氧基苯基)(苯基)甲烷及其合成方法 Download PDFInfo
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- C07C41/01—Preparation of ethers
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Abstract
本发明公开了一种(2‑羟基苯基)(2,4,6‑三甲氧基苯基)(苯基)甲烷及其合成方法,它由水杨醛、苯硼酸和三甲氧基苯,使用FeCl3或者I2“一锅”反应合成得到。这三种不同的芳基是在不含碱/配体的条件下,从价格低廉且容易获得的芳烃一步引入的,该反应具有很高的化学选择性,合成方法操作简便,反应时间短,两种催化剂都廉价易得,生产成本低,污染少,后处理简单,而且反应具有很好的收率。
Description
技术领域
本发明属于有机合成技术领域,具体来说涉及一种(2-羟基苯基)(2,4,6-三甲氧基苯基)(苯基)甲烷及其合成方法。
背景技术
(2-羟基苯基)(2,4,6-三甲氧基苯基)(苯基)甲烷属于三芳基甲烷衍生物,三芳基甲烷衍生物由于其结构的特殊性,被广泛应用于医药化学、染料工业和材料科学中,是一类非常重要的化合物。到目前为止,合成三芳基甲烷衍生物常用的方法主要是:通过傅克烷基化法,由二芳基甲醇(酯、醚、亚胺等)直接与芳烃发生反应,这种合成方法一般是对芳烃含有给电子基团的容易反应,反应底物有一定的局限性,而且容易有异构体副产物;另一种合成方法是通过交叉偶联反应或者是过渡金属催化的碳-氢官能化反应合成得到;还有一种方法是通过对苯醌衍生物的1,6-加成芳基化反应来合成。在上述合成方法中有一些明显的不足之处,例如:有限的反应底物范围,较差的区域选择性,反应中常常用到昂贵的过渡金属,需要多步反应和严苛的反应条件等。
发明内容
针对现有技术的不足,本发明的目的在于提供一种(2-羟基苯基)(2,4,6-三甲氧基苯基)(苯基)甲烷的合成方法。
本发明的另一目的是提供上述合成方法获得的(2-羟基苯基)(2,4,6-三甲氧基苯基)(苯基)甲烷。
本发明的目的是通过下述技术方案予以实现的。
一种(2-羟基苯基)(2,4,6-三甲氧基苯基)(苯基)甲烷的合成方法,包括以下步骤:
将第一反应物、第二反应物、第三反应物、哌啶和催化剂混合,再加入溶剂,在40~120℃搅拌条件下反应20~80min,反应结束后冷却至室温20~25℃,再加入乙酸乙酯,洗涤,得到有机相,对所述有机相进行干燥,蒸除溶剂后,得到残余物,将所述残余物经柱层析分离,再次蒸除溶剂,干燥得到(2-羟基苯基)(2,4,6-三甲氧基苯基)(苯基)甲烷,其中,按物质的量计,所述第一反应物、第二反应物、第三反应物、哌啶和催化剂的比为1:(1~1.5):(1~1.5):(1~1.5):(0.5~1),所述催化剂为I2或FeCl3;
在上述技术方案中,采用正己烷和乙酸乙酯的混合液作为柱层析分离的洗脱剂,按体积份数计,所述正己烷和乙酸乙酯的比6:1。
在上述技术方案中,所述溶剂为1,4-二氧六环、氯苯、乙睛、乙醇、二氯乙烷和二甲基甲酰胺的一种以上,用于为第一反应物、第二反应物、哌啶和第三反应物提供均匀分散的氛围。
在上述技术方案中,所述溶剂为1,4-二氧六环、氯苯、乙睛、乙醇、二氯乙烷或二甲基甲酰胺。
在上述技术方案中,所述乙酸乙酯的体积份数与所述第一反应物的物质的量份数的比为(30~50):1。
在上述技术方案中,所述洗涤为先后依次用水和饱和食盐水洗涤。
在上述技术方案中,所述第一反应物的物质的量份数与所述溶剂的体积份数的比为1:(1~2),当所述物质的量份数的单位为mmol时,所述体积份数的单位为mL。
在上述技术方案中,优选在120℃搅拌反应20~80min。
在上述技术方案中,采用薄层色谱法检测确定搅拌条件下反应的时间。
在上述技术方案中,对所述有机相进行干燥的操作步骤为:向所述有机相中加入无水硫酸钠进行干燥,过滤无水硫酸钠。
上述合成方法获得的(2-羟基苯基)(2,4,6-三甲氧基苯基)(苯基)甲烷。
与现有技术相比,本发明合成方法具有的优点和特点如下:
1、合成步骤简单,反应时间短,收率高,反应原料以及所使用的催化剂廉价易得,本发明为无金属催化的反应条件;
2、本发明的合成方法为“一锅”反应,反应后处理简单:反应结束后,通过简单的过滤,经柱层析分离得产品。
具体实施方式
在本发明的具体实施方式中,合成方法所涉及的试剂以及药品均为商业途径购买,均购买自天津试剂六厂,药品纯度均为分析纯,试剂和药品都是直接使用,没有经过任何前处理。
本发明的合成方法全程持续搅拌,搅拌所使用的电磁加热搅拌器的型号为NUOVAII(美国特马兰公司);旋转蒸发仪的型号为RE-2000A(巩义市予华仪器责任有限公司)。核磁共振仪器型号:Bruker AV-400 spectrometer,400MHz。
在下述实施例中,在加热回流反应时,通过薄层色谱法(TLC)检测反应进行的程度。在薄层色谱法中,使用尺寸为15mm×50mm的G254型硅胶板,所使用ZF-I型三用紫外分析仪(上海驰唐),所使用药品购买自天津试剂六厂,药品纯度都为分析纯,全部都是直接使用,没有经过任何前处理。通过TLC检测发现原料水杨醛消失,并且只有目标化合物点时,标志本发明的合成方法反应结束,可以继续进行下一步的分离操作。
在下述实施例中,室温为20~25℃。当柱层析分离时,展开剂极性:正己烷/乙酸乙酯=6:1(按体积份数计)。
有机相经无水硫酸钠干燥、过滤:向有机相中加入无水硫酸钠进行干燥,过滤无水硫酸钠。
在本发明的具体实施方式中,物质的量的单位为mmol,体积的单位为ml。
在下述实施例中,均有两次减压蒸除溶剂,第一次减压蒸除为尽量将所有的溶剂蒸除(可能会有残余),第二次将剩余的全部溶剂蒸除(第一次蒸除溶剂的体积与第二次蒸除溶剂的体积比不影响下述实施例获得目标化合物的效果)。
下面结合具体实施例进一步说明本发明的技术方案。
实施例1
(2-羟基苯基)(2,4,6-三甲氧基苯基)(苯基)甲烷的合成方法,包括以下步骤:
依次将1.0mmol(0.122g)水杨醛、1.0mmol(0.122g)苯硼酸、1.2mmol(0.102g)哌啶、1.2mmol(0.202g)1,3,5-三甲氧基苯和0.5mmol(0.127g)催化剂I2加入10ml干燥的圆底烧瓶内,再加入1ml氯苯作溶剂,120℃加热回流反应,TLC监测反应,待反应完全后,冷却至室温,向反应体系中加入30ml乙酸乙酯,依次用20ml水和10ml饱和食盐水洗涤,有机相经无水硫酸钠干燥、过滤,减压蒸除大量溶剂后,将残余物经柱层析分离,采用正己烷和乙酸乙酯作为洗脱剂,将溶剂蒸除干净,干燥即得到目标化合物,反应收率59%,1H NMR(400MHz,CDCl3):δ=3.73(s,6H,CH3),3.86(s,3H,CH3),6.15(s,1H,CH),6.25(s,2H,ArH),6.58(s,1H,ArH),6.88-6.92(m,2H,ArH),7.16-7.30(m,7H,ArH).13C NMR(100MHz,CDCl3):δ=40.6,55.4,55.9,91.9,110.7,116.3,119.7,125.7,127.6,127.9,128.1,128.3,131.9,141.5,154.9,158.6,160.5.
实施例2
(2-羟基苯基)(2,4,6-三甲氧基苯基)(苯基)甲烷的合成方法,包括以下步骤:
依次将1.0mmol(0.122g)水杨醛、1.0mmol(0.122g)苯硼酸、1.2mmol(0.102g)哌啶、1.2mmol(0.202g)1,3,5-三甲氧基苯和1mmolFeCl3(催化剂)(0.161g)加入10ml干燥的圆底烧瓶内,再加入2ml氯苯作溶剂,120℃加热回流反应,TLC监测反应,待反应完全后,冷却至室温,向反应体系中加入50ml乙酸乙酯,依次用30ml水和饱和食盐水洗涤,有机相经无水硫酸钠干燥、过滤,减压蒸除大量溶剂后,将残余物经柱层析分离,采用正己烷和乙酸乙酯作为洗脱剂,将溶剂蒸除干净,干燥即得到目标化合物,反应收率78%。1H NMR(400MHz,CDCl3):δ=3.66(s,6H,CH3),3.79(s,3H,CH3),6.08(s,1H,CH),6.18(s,2H,ArH),6.55(s,1H,ArH),6.79-6.85(m,2H,ArH),7.11-7.18(m,4H,ArH),7.22-7.25(m,3H,ArH).13C NMR(100MHz,CDCl3):δ=40.6,55.4,55.9,91.9,110.7,116.3,119.7,125.7,127.6,127.9,128.1,128.3,131.9,141.5,154.9,158.6,160.5.
各实施例所得纯的(2-羟基苯基)(2,4,6-三甲氧基苯基)(苯基)甲烷的核磁共振氢谱的各个氢化学位移结果的准确归属以及碳谱碳原子的信号归属,证实本发明所合成的目标化合物为(2-羟基苯基)(2,4,6-三甲氧基苯基)(苯基)甲烷。
以上对本发明做了示例性的描述,应该说明的是,在不脱离本发明的核心的情况下,任何简单的变形、修改或者其他本领域技术人员能够不花费创造性劳动的等同替换均落入本发明的保护范围。
Claims (10)
1.一种(2-羟基苯基)(2,4,6-三甲氧基苯基)(苯基)甲烷的合成方法,其特征在于,包括以下步骤:
将第一反应物、第二反应物、第三反应物、哌啶和催化剂混合,再加入溶剂,在40~120℃搅拌条件下反应20~80min,反应结束后冷却至室温20~25℃,再加入乙酸乙酯,洗涤,得到有机相,对所述有机相进行干燥,蒸除溶剂后,得到残余物,将所述残余物经柱层析分离,再次蒸除溶剂,干燥得到(2-羟基苯基)(2,4,6-三甲氧基苯基)(苯基)甲烷,其中,按物质的量计,所述第一反应物、第二反应物、第三反应物、哌啶和催化剂的比为1:(1~1.5):(1~1.5):(1~1.5):(0.5~1),所述催化剂为I2或FeCl3;
2.根据权利要求1所述的合成方法,其特征在于,所述乙酸乙酯的体积份数与所述第一反应物的物质的量份数的比为(30~50):1。
3.根据权利要求2所述的合成方法,其特征在于,所述溶剂为1,4-二氧六环、氯苯、乙睛、乙醇、二氯乙烷和二甲基甲酰胺的一种以上,用于为第一反应物、第二反应物、哌啶和第三反应物提供均匀分散的氛围。
4.根据权利要求2所述的合成方法,其特征在于,所述溶剂为1,4-二氧六环、氯苯、乙睛、乙醇、二氯乙烷或二甲基甲酰胺。
5.根据权利要求3或4所述的合成方法,其特征在于,采用正己烷和乙酸乙酯的混合液作为柱层析分离的洗脱剂,按体积份数计,所述正己烷和乙酸乙酯的比6:1。
6.根据权利要求5所述的合成方法,其特征在于,所述洗涤为先后依次用水和饱和食盐水洗涤;
所述第一反应物的物质的量份数与所述溶剂的体积份数的比为1:(1~2),当所述物质的量份数的单位为mmol时,所述体积份数的单位为mL。
7.根据权利要求6所述的合成方法,其特征在于,优选在120℃搅拌反应20~80min。
8.根据权利要求7所述的合成方法,其特征在于,采用薄层色谱法检测确定搅拌条件下反应的时间。
9.根据权利要求8所述的合成方法,其特征在于,对所述有机相进行干燥的操作步骤为:向所述有机相中加入无水硫酸钠进行干燥,过滤无水硫酸钠。
10.如权利要求1~9中任意一项所述合成方法获得的(2-羟基苯基)(2,4,6-三甲氧基苯基)(苯基)甲烷。
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