联萘二烷基醚的合成
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摘要
采用Williamson醚合成法,以联萘酚和溴代烷为原料,在碱性条件下,并以四丁基溴化铵为相转移催化剂合成系列联萘二烷基醚化合物。通过薄层层析(TLC)技术对反应进程及产品的纯度进行分析。本实验包括回流、重结晶、干燥、TLC等实验操作以及熔点测定、红外光谱、核磁共振等检测方法。该实验具有原料易得、产品易分离且纯度及产率高等优点,是一个适用于本科生的有机化学实验。
A series of 2,2'-dialkoxy-1,1'-binaphthyl was synthesized with 2,2'-dihydroxy-1,1'-binaphthyl,n-alkyl bromide and sodium hydroxide as starting materials and tetrabutylammonium bromide(TBAB) as phase transfer catalyst by the method of Williamson ether synthesis. The experiment introduces students to various hands-on experimental organic synthetic techniques, such as reflux, washing, recrystallization, drying, thin layer chromatography(TLC), and characterizing final products by melting point, IR and NMR spectroscopy. The starting materials for reaction are commercially available, and the products can be readily isolated by simple filtration, as well as the final products in high yield with high purity. The experimental results show that the process is in accordance with the requirements of organic chemistry laboratory teaching.
A series of 2,2'-dialkoxy-1,1'-binaphthyl was synthesized with 2,2'-dihydroxy-1,1'-binaphthyl,n-alkyl bromide and sodium hydroxide as starting materials and tetrabutylammonium bromide(TBAB) as phase transfer catalyst by the method of Williamson ether synthesis. The experiment introduces students to various hands-on experimental organic synthetic techniques, such as reflux, washing, recrystallization, drying, thin layer chromatography(TLC), and characterizing final products by melting point, IR and NMR spectroscopy. The starting materials for reaction are commercially available, and the products can be readily isolated by simple filtration, as well as the final products in high yield with high purity. The experimental results show that the process is in accordance with the requirements of organic chemistry laboratory teaching.
引文
[1] Williamson A.Ueber die Theorie der Aetherbildung [J].European Journal of Organic Chemistry,1851,77 (1):37-49.
[2] 张文勤,郑艳,马宁,等.有机化学 [M].5版.北京:高等教育出版社,2014.
[3] Ouk S,Thiebaud S,Borredon E,et al.Dimethyl carbonate and phenols to alkyl aryl ethers via clean synthesis [J].Green Chemistry,2002,4 (5):431-435.
[4] Bauer T,Gajewiak J.Diastereoselective synthesis of 2-alkoxy-5-tert-butylmandelic acid [J].Synthesis-Stuttgart,2004 (1):20-22.
[5] Wünsche Ch,Sachs A,Mayer W.Elektronenstoss-induzierte alkyl-und wasserstoffwanderung-II[J].Tetrahedron,1969,25(1):73-87.
[6] Mandal S,Mandal S,Ghosh SK,et al.A review on theadvancement of ether synthesis from organic solvent to water [J].RSC Advances,2016(73):69605-69614.
[7] Mitsunobu O.Yamada M,Mukaiyama T.Preparation of Esters of Phosphoric Acid by the Reaction of Trivalent Phosphorus Compounds with Diethyl Azodicarboxylate in the Presence of Alcohols [J].Bulletin of the Chemical Society of Japan 1967,40 (4):935-939.
[8] Mitsunobu,O.;Yamada,M.Preparation of Esters of Carboxylic and Phosphoric Acid via Quaternary Phosphonium Salts [J].Bulletin of the Chemical Society of Japan,1967,40 (10):2380-2382.
[2] 张文勤,郑艳,马宁,等.有机化学 [M].5版.北京:高等教育出版社,2014.
[3] Ouk S,Thiebaud S,Borredon E,et al.Dimethyl carbonate and phenols to alkyl aryl ethers via clean synthesis [J].Green Chemistry,2002,4 (5):431-435.
[4] Bauer T,Gajewiak J.Diastereoselective synthesis of 2-alkoxy-5-tert-butylmandelic acid [J].Synthesis-Stuttgart,2004 (1):20-22.
[5] Wünsche Ch,Sachs A,Mayer W.Elektronenstoss-induzierte alkyl-und wasserstoffwanderung-II[J].Tetrahedron,1969,25(1):73-87.
[6] Mandal S,Mandal S,Ghosh SK,et al.A review on theadvancement of ether synthesis from organic solvent to water [J].RSC Advances,2016(73):69605-69614.
[7] Mitsunobu O.Yamada M,Mukaiyama T.Preparation of Esters of Phosphoric Acid by the Reaction of Trivalent Phosphorus Compounds with Diethyl Azodicarboxylate in the Presence of Alcohols [J].Bulletin of the Chemical Society of Japan 1967,40 (4):935-939.
[8] Mitsunobu,O.;Yamada,M.Preparation of Esters of Carboxylic and Phosphoric Acid via Quaternary Phosphonium Salts [J].Bulletin of the Chemical Society of Japan,1967,40 (10):2380-2382.