CN113004169A - 一种1,3-二苯基-2-丁烯-1-酮o-正丁基肟的制备方法 - Google Patents
一种1,3-二苯基-2-丁烯-1-酮o-正丁基肟的制备方法 Download PDFInfo
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Abstract
一种1,3‑二苯基‑2‑丁烯‑1‑酮O‑正丁基肟的制备方法,其属于有机合成技术领域。该方法以苯乙酮为起始原料,滴加二氯亚砜,在二氯亚砜的催化下进行无溶剂反应后,经过淬灭、洗涤、萃取减压蒸馏即可得到纯化的1,3‑二苯基‑2‑丁烯‑1‑酮。将盐酸羟胺、氢氧化钾、溴代正丁烷、乙醇、水依次加入所得的1,3‑二苯基‑2‑丁烯‑1‑酮粗产品中于室温下反应,所得的产品进行减压脱溶,得1,3‑二苯基‑2‑丁烯‑1‑酮O‑正丁基肟。采用本发明方法可以在常规条件下制备1,3‑二苯基‑2‑丁烯‑1‑酮O‑正丁基肟,中间体不需要分离提纯,操作安全、简单,节省能源。该方法起始原料廉价,有利于降低生产成本。工艺过程简单,能耗少,操作方便,适宜于产业化规模生产。
Description
技术领域
本发明涉及一种O-正丁基肟类化合物的合成方法,特别是1,3-二苯基-2-丁烯-1-酮 O-正丁基肟的制备方法,其属于有机合成技术领域。
背景技术
1,3-二苯基-2-丁烯-1-酮 O-正丁基肟,其分子式为C20H23NO, 其化学式如式S-1所示;为一种O-正丁基肟类化合物。
S-1
目前,关于1,3-二苯基-2-丁烯-1-酮 O-正丁基肟及其合成方法,尚未文献报道。
通过查阅文献,发现其类似物苯乙酮O-正丁基肟及取代苯乙酮O-正丁基肟的制备方法主要有以下几种:
1) Li[1]等人报道了一种以苯乙酮、盐酸羟胺和溴代正丁烷为原料在KOH碱性条件下一步法制备苯乙酮O-正丁基肟的方法,如式S-2所示:
2) Shinozaki, Hiraku[2] et al和Abele, Edgars[3] et al等人通过苯乙酮肟与溴代正丁烷/氯代正丁烷在碱催化下制备出苯乙酮O-正丁基肟,如式S-3、S-4所示:
3)In, Gyeong Su[4] et al和Shioda, Takayuki[5]等人提出一种利用正丁氧基胺盐酸盐和取代苯乙酮在室温下反应生成取代苯乙酮O-正丁基肟的方法。如式S-5、S-6所示:
S-2
S-3
S-4
S-5
S-6
上述方法存在这以下缺陷:
Li等人合成苯乙酮O-正丁基肟的方法,其过程需要在较高温度下进行,对设备的要求较高,且需要外部供给能量保证反应所需温度,导致生产成本增加。Shinozaki Hiraku和Abele Edgars等人的制备方法中利用苯乙酮肟作为生产苯乙酮O-正丁基肟的原料,原料价格较为昂贵,会导致成本增加且氯代正丁烷制备苯乙酮O-正丁基肟的产率较低,不适用于化工生产。In Gyeong Su和Shioda Takayuki等人的制备方法中,正丁基胺盐酸盐价格昂贵,不适用于大规模生产。
参考文献:
[1] Li Chunbao, Zhang Hang, Cui Yi. One-pot synthesis of oxime ethersfrom benzaldehyde or acetophenone, hydroxylamine salt, potassium hydroxide,and alkyl halides[J] Synthetic Communications, 2003, 33, 543-546.
[2] Shinozaki Hiraku, Yoshida Noyuki. The preparation of oxime ethersunder phase transfer conditions[J] Chemistry Letters, 1980, 7, 869-870.
[3] Abele Edgars, Abele Ramona. Alkylation of aryl and hetaryl ketoximeswith alkyl iodides prepared in situ from alkyl chlorides under phase transfercatalysis conditions[J] Synthetic Communications. 1998, 14, 2621-2633.
[4] In, Gyeong Su; Kim, Nam Jung. Bis(4-hydroxy)benzophenone oxime ethercompounds as estrogen receptor agonists, and method for the preparationthereof: KR2017052873[P]. 2015-11-05.
[5] Shioda Takayuki, Arimori Sadayuki. Preparation of tetrazolinonecompounds as pesticides: WO2014104384[P]. 2003-12-24。
发明内容
本发明要解决的技术问题是提供一种1,3-二苯基-2-丁烯-1-酮O-正丁基肟及其制备方法,具有原料低廉易得,成本低廉等特点。
为了解决上述技术问题,本发明提供了1,3-二苯基-2-丁烯-1-酮O-正丁基肟,其结构式为:
本发明还同时提供1,3-二苯基-2-丁烯-1-酮 O-正丁基肟的制备方法,包括如下步骤:
1)1,3-二苯基-2-丁烯-1-酮的制备:
将苯乙酮置于反应器中,滴加二氯亚砜,从而使得苯乙酮在二氯亚砜催化作用下在无溶剂下室温反应,苯乙酮与二氯亚砜的摩尔比为1:1.4~1:1.8(最佳为1:1.6~1:1.7);二氯亚砜的滴加时间为0.5-1h;滴加至反应体系溶液颜色变为深红色;继续在室温下反应2~4h;
备注说明:反应过程(整个反应过程,主要包括滴加过程)中用碱性溶液吸收所产的HCl、SO2酸性气体。
2)、1,3-二苯基-2-丁烯-1-酮的萃取:
将步骤1)的反应液用饱和碳酸钠水溶液或者碳酸钾、碳酸氢钠、氢氧化钠、氢氧化钾水溶液中和;用乙酸乙酯萃取三次,合并有机相;用无水硫酸镁或者硫酸钠干燥。
3)、1,3-二苯基-2-丁烯-1-酮减压蒸馏纯化:
将步骤2)的反应产物在133 Pa、170℃条件下减压蒸馏,将1,3-二苯基-2-丁烯-1-酮馏出得到淡黄色液体。
4)、1,3-二苯基-2-丁烯-1-酮 O-正丁基肟的制备:
将步骤3)所得的1,3-二苯基-2-丁烯-1-酮纯化产品置于反应器中,依次加入盐酸羟胺、氢氧化钾、溴代正丁烷、乙醇、水于室温下反应10h;1,3-二苯基-2-丁烯-1-酮、盐酸羟胺、和溴代正丁烷的摩尔比为1:1.25:1.25;水和乙醇的体积比为2.5:1;氢氧化钾与水的质量比为1:1;
备注说明:反应过程中,体系一直要保持碱性状态。
5)、1,3-二苯基-2-丁烯-1-酮 O-正丁基肟减压蒸馏纯化:
将步骤4)所得反应产物减压脱溶,得1,3-二苯基-2-丁烯-1-酮 O-正丁基肟,其性状为淡黄色油状液体。
本发明的合成过程如式S-7所示。
S-7
本发明的有益效果为:该方法合成了一种新型的化合物1,3-二苯基-2-丁烯-1-酮O-正丁基肟,该方法具有以下优点:
1、起始原料廉价并且已经产业化,有利于保证原料的供应,降低生产成本。
2、中间体不需要分离提纯,操作安全、简单,节省能源。
3、各反应工艺过程简单,能耗少,操作方便,适宜于产业化规模生产。
附图说明
下面结合附图对本发明的具体实施方式作进一步详细说明。
图1 为1,3-二苯基-2-丁烯-1-酮的1H -NMR图:1H- NMR (600 MHz, DMSO) δ11.21 (s, 1H), 7.60 (t, J = 8.1 Hz, 4H), 7.38 (m, 4H), 7.32 (m, 2H), 6.63 (s,1H), 1.79 (s, 3H)。
图2 为1,3-二苯基-2-丁烯-1-酮的MS图:M/z: 221.1 (20)。
图3 为1,3-二苯基-2-丁烯-1-酮O-正丁基肟的1H -NMR图:1H NMR (600 MHz,DMSO) δ 7.59 (d, J = 6.6 Hz, 4H), 7.41 (m, 4H), 7.35 (t, J = 7.42 Hz, 2H),6.60 (s, 1H), 4.17 (t, J = 6.6 Hz, 2H), 1.80 (s, 3H), 1.64 (m, 2H), 1.34 (m,2H), 0.91 (t, J = 7.4 Hz, 3H)。
图4 为1,3-二苯基-2-丁烯-1-酮 O-正丁基肟的MS图:M/z:293.2 (100), 295.2(20),296.2(5)。
具体实施方式
以下通过实例进一步描述本发明。不过这些实施例仅仅是范例性的,并不对本发明的保护范围构成任何限制。下述非限制性实施例可以使本领域的普通技术人员更全面的理解本发明,但不以任何方式限制本发明。下述实施例中,如无特殊说明,所使用的实验方法均为常规方法,所用材料、试剂等均可从化学试剂公司购买。
实施例1
250mL三口烧瓶中加入磁力搅拌子,安装温度计,恒压滴液漏斗,加入苯乙酮18g(0.15mol),无水乙醇34.5g,用冰盐浴维持反应温度在0摄氏度以下,缓慢滴加二氯亚砜14.8 mL(0.21 mol),当溶液变成深红色时,继续在室温下反应2~4h;用饱和碳酸钠将反应液中和至中性,加入乙酸乙酯(100 mL)萃取三次,合并有机相,将有机相在无水硫酸钠中干燥过夜,在133 Pa、170℃条件下减压蒸馏,得到淡黄色液体1,3-二苯基-2-丁烯-1-酮(产率:74%)。
实施例2
250mL三口烧瓶中加入磁力搅拌子,安装温度计,恒压滴液漏斗,加入苯乙酮18g(0.15mol),无水乙醇34.5g,用冰盐浴维持反应温度在0摄氏度以下,缓慢滴加二甲基亚砜17.7mL(0.25 mol),当溶液变成深红色时,继续在室温下反应2~4h;用饱和碳酸钠将反应液中和至中性,加入乙酸乙酯(100 mL)萃取三次,合并有机相,将有机相在无水硫酸钠中干燥过夜,在133 Pa、170℃条件下减压蒸馏,得到淡黄色液体1,3-二苯基-2-丁烯-1-酮(产率:85%)。
实施例3
250mL三口烧瓶中加入磁力搅拌子,安装温度计,恒压滴液漏斗,加入苯乙酮18g(0.15mol),无水乙醇34.5g,用冰盐浴维持反应温度在0摄氏度以下,缓慢滴加二甲基亚砜19.08mL(0.27 mol),当溶液变成深红色时,继续在室温下反应2~4h;用饱和碳酸钠将反应液中和至中性,加入乙酸乙酯(100 mL)萃取三次,合并有机相,将有机相在无水硫酸钠中干燥过夜,在133 Pa、170℃条件下减压蒸馏,得到淡黄色液体1,3-二苯基-2-丁烯-1-酮(产率:80%)。
实施例4
500mL三口烧瓶中加入磁力搅拌子,加入1,3-二苯基-2-丁烯-1-酮26.24g,盐酸羟胺10.7g,250mL乙醇,吡啶,溴代正丁烷,水100mL,室温搅拌20h,用饱和碳酸钠将反应液中和至中性,加入乙酸乙酯(100mL)萃取三次,合并有机相,将有机相在无水硫酸钠中干燥过夜,减压脱溶,得到淡黄色液体1,3-二苯基-2-丁烯-1-酮O-正丁基肟18.7 g(产率:54%)。
实施例5
500mL三口烧瓶中加入磁力搅拌子,加入1,3-二苯基-2-丁烯-1-酮26.24g,盐酸羟胺10.7g,250mL乙醇,氢氧化钾,溴代正丁烷,水100mL,室温搅拌20h,用饱和碳酸钠将反应液中和至中性,加入乙酸乙酯(100mL)萃取三次,合并有机相,将有机相在无水硫酸钠中干燥过夜,减压脱溶,得到淡黄色液体1,3-二苯基-2-丁烯-1-酮 O-正丁基肟30.47g,可得在氢氧化钾催化条件下产量较高(产率:88%)。
Claims (2)
1.一种1,3-二苯基-2-丁烯-1-酮O-正丁基肟的制备方法,其特征是:1,3-二苯基-2-丁烯-1-酮O-正丁基肟的结构式为:
1,3-二苯基-2-丁烯-1-酮O-正丁基肟的制备方法,包括如下步骤:
1)1,3-二苯基-2-丁烯-1-酮的制备:
将苯乙酮置于反应器中,滴加二氯亚砜,从而使得苯乙酮在二氯亚砜催化作用下在无溶剂下室温反应,苯乙酮与二氯亚砜的摩尔比为1:1.4-1:1.8;二氯亚砜的滴加时间为0.5-1h;滴加至反应体系溶液颜色变为深红色,继续在室温下反应2-4h;
2)1,3-二苯基-2-丁烯-1-酮的萃取:
将步骤1)的反应液用碳酸钾、碳酸氢钠、氢氧化钠、氢氧化钾的水溶液或者饱和碳酸钠水溶液中和;用乙酸乙酯萃取,合并有机相;用无水硫酸镁或者硫酸钠干燥;
3)1,3-二苯基-2-丁烯-1-酮减压蒸馏纯化:
将步骤2)的反应产物在133 Pa、170℃条件下减压蒸馏,将1,3-二苯基-2-丁烯-1-酮馏出得到淡黄色液体;
4)1,3-二苯基-2-丁烯-1-酮 O-正丁基肟的制备:
将步骤3)所得的1,3-二苯基-2-丁烯-1-酮纯化产品置于反应器中,依次加入盐酸羟胺、氢氧化钾、溴代正丁烷、乙醇、水于室温下反应10h;1,3-二苯基-2-丁烯-1-酮、盐酸羟胺和溴代正丁烷的摩尔比为1:1.25:1.25;水和乙醇的体积比为2.5:1;氢氧化钾与水的质量比为1:1;
5)1,3-二苯基-2-丁烯-1-酮 O-正丁基肟减压蒸馏纯化:
将步骤4)所得反应产物减压脱溶,得1,3-二苯基-2-丁烯-1-酮 O-正丁基肟,其性状为淡黄色油状液体。
2.根据权利要求1所述的1,3-二苯基-2-丁烯-1-酮O-正丁基肟的制备方法,其特征在于:步骤1中苯乙酮与二氯亚砜的摩尔比为1:1.6-1:1.7。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4237326A (en) * | 1979-05-30 | 1980-12-02 | Mitsubishi Petrochemical Company Limited | Method of inhibiting polymerization of styrene |
CN101265212A (zh) * | 2008-03-27 | 2008-09-17 | 上海交通大学 | 可用于抗肿瘤的紫草酮肟衍生物 |
CN102307850A (zh) * | 2009-02-10 | 2012-01-04 | 日本曹达株式会社 | 含氮化合物和有害生物防除剂 |
WO2017024971A1 (zh) * | 2015-08-12 | 2017-02-16 | 沈阳中化农药化工研发有限公司 | 一种不饱和肟醚类化合物及其用途 |
CN109761926A (zh) * | 2019-01-16 | 2019-05-17 | 华南理工大学 | 一种β-异恶唑酮/醛的合成方法 |
-
2020
- 2020-10-14 CN CN202011093345.8A patent/CN113004169A/zh active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4237326A (en) * | 1979-05-30 | 1980-12-02 | Mitsubishi Petrochemical Company Limited | Method of inhibiting polymerization of styrene |
CN101265212A (zh) * | 2008-03-27 | 2008-09-17 | 上海交通大学 | 可用于抗肿瘤的紫草酮肟衍生物 |
CN102307850A (zh) * | 2009-02-10 | 2012-01-04 | 日本曹达株式会社 | 含氮化合物和有害生物防除剂 |
WO2017024971A1 (zh) * | 2015-08-12 | 2017-02-16 | 沈阳中化农药化工研发有限公司 | 一种不饱和肟醚类化合物及其用途 |
CN109761926A (zh) * | 2019-01-16 | 2019-05-17 | 华南理工大学 | 一种β-异恶唑酮/醛的合成方法 |
Non-Patent Citations (2)
Title |
---|
LI CHUNBAO 等: "One-Pot Synthesis of Oxime Ethers from Benzaldehyde or Acetophenone, Hydroxylamine Salt, Potassium Hydroxide, and Alkyl Halides", 《SYNTHETIC COMMUNICATIONS》 * |
LUO GUOYONG等: "Access to Cyclic b-Amino Acids by Amine-Catalyzed Enantioselective Addition of the g-Carbon Atoms of a,b-Unsaturated Imines to Enals", 《ANGEWANDTE CHEMIE INTERNATIONAL EDITION》 * |
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