856816-70-1Relevant academic research and scientific papers
Synthesis of chloroesters by the reaction of ethers with acyl chlorides catalyzed by ZnO
Tang, Yuqi,Feng, Chengliang,Yang, Wanfeng,Ji, Min,Wang, Wei,Chen, Junqing
, p. 1 - 8 (2020/07/13)
An efficient method for the synthesis of chloroesters by the reaction of ethers with acyl chlorides catalyzed by nano-ZnO under solvent-free condition at room temperature was described. The method is compatible with a range of ethers including tricyclic ethers, tetracyclic ethers, pentacyclic ethers and hexacyclic ethers and have afforded the products with moderate to good yields. The ZnO could be reused up to three times and the product yield after three cycles is 87%.
Synthesis of Vicinal Dichlorides via Activation of Aliphatic Terminal Epoxides with Triphosgene and Pyridine
Cleveland, Alexander H.,Fronczek, Frank R.,Kartika, Rendy
, p. 3367 - 3377 (2018/03/26)
Herein we report a novel synthetic reaction to convert unactivated terminal aliphatic epoxide to alkyl vicinal dichloride based on triphosgene-pyridine activation. Our methodology is operationally simple and readily tolerated by a broad of scope of substrates as well as protecting groups. Furthermore, these mild conditions generally yield clean reaction mixtures that are free of byproducts upon aqueous workup.
An efficient iron catalyzed regioselective acylative cleavage of ethers: Scope and mechanism
Bodduri, V.D. Vijaykumar,Choi, Kyung-Min,Vaidya, Raghavender Rao,Patil, Kalpesh,Chirumarry, Sridhar,Jang, Kiwan,Yoon, Yong-Jin,Falck, John R.,Shin, Dong-Soo
supporting information, p. 7089 - 7093 (2015/12/01)
A method involving iron catalyzed acylative cleavage of cyclic and acyclic ethers with acyl/aroyl chlorides has been studied to produce chloroesters and esters respectively. Examination of the scope revealed that less electron rich alkyl group in unsymmetric, acyclic ether was acylated while the chloride derived from the counterpart moiety was volatile and difficult to isolate. In contrast, α-branched cyclic ethers were converted to the corresponding primary ester and secondary chloride. Steric hindrance of ether also plays an important role in acylative C-O bond cleavage. The mechanism of ether cleavage is proposed to involve a single electron initiated SN1 dissociative pathway.
Combining AlCl3·6H2O and an ionic liquid to prepare chlorohydrin esters from glycerol
Villorbina, Gemma,Tomàs, Albert,Escribà, Marc,Oromí-Farrús, Mireia,Eras, Jordi,Balcells, Mercè,Canela, Ramon
experimental part, p. 2828 - 2830 (2009/09/30)
We describe here the first example in which glycerol has been transformed into chlorohydrin esters using an ionic liquid and hydrated aluminium chloride. The method avoids using Crown-18 ether, which was needed to obtain a similar yield when KCl was used.
From glycerol to chlorohydrin esters using a solvent-free system. Microwave irradiation versus conventional heating
Escribà, Marc,Eras, Jordi,Duran, Miquel,Simon, Sílvia,Butchosa, Cristina,Villorbina, Gemma,Balcells, Mercè,Canela, Ramon
experimental part, p. 10370 - 10376 (2010/02/27)
Esterification-chlorination of glycerol provides chlorohydrin esters in high yields. A ratio of reagents close to equivalence can be used, so that atom economy of the reaction is optimized. The reaction can be carried out using either classical or microwa
A mild and efficient synthesis of chloroesters by the cleavage of cyclic and acyclic ethers using Bi(NO3)3·5H2O as a catalyst under solvent-free conditions
Suresh,Suryakiran,Venkateswarlu
, p. 1037 - 1040 (2008/09/16)
A facile, efficient synthesis of chloroesters is described. The reaction of cyclic and acyclic ethers with acid chlorides in the presence of catalytic amounts of Bi(NO3)2·5H2O under solvent-free conditions yielded the corresponding chloroesters. Also, the catalyst can be recovered conveniently and reused efficiently for at least six times.
Mild and efficient method for the cleavage of cyclic and acyclic ethers by iodine under solvent-free conditions
Yadav,Reddy,Reddy, P. Murali Krishna,Gupta, Manoj K.
, p. 8493 - 8495 (2007/10/03)
Ethers undergo smooth cleavage with acyl chlorides in the presence of a catalytic amount of elemental iodine under extremely mild conditions to give the corresponding halo esters. This new procedure offers significant advantages such as high conversions, short reaction times and enhanced selectivity together with mild reaction conditions, which makes it an attractive strategy.
