946-02-1Relevant articles and documents
One-pot synthesis of ω-chloroesters via the reaction of acid chlorides with tetrahydrofuran in the presence of trichloroborane
Malladi, Rama R.,Kabalka, George W.
, p. 1997 - 2001 (2002)
The reaction of acid chlorides with tetrahydrofuran in the presence of trichloroborane produces ω-chloroesters in excellent yields.
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%.
Preparation method of p-phenylbutoxybenzoic acid
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Paragraph 0043-0046, (2020/07/24)
The invention discloses a preparation method of p-phenylbutoxybenzoic acid. The preparation method comprises the following steps: using tetrahydrofuran as an initial raw material; carrying out a catalytic reaction with benzoyl chloride to prepare 4-chlorobutanol benzoate; carrying out a Friedel-Crafts alkylation reaction and hydrolysis on 4-chlorobutanol benzoate and benzene to obtain 4-phenylbutanol, carrying out a reaction on the 4-phenylbutanol and thionyl chloride to obtain 4-phenylchlorobutane, carrying out an alkylation reaction on the 4-phenylchlorobutane and methyl p-hydroxybenzoate under the action of potassium carbonate to obtain methyl p-phenylbutoxybenzoate. The raw materials used in the invention are cheap and easily available, the process is easy to realize industrialization,and the obtained final product has the advantages of high purity, novel route, short synthesis route, no dangerous process and simple equipment.
Synthesis, in silico study and antimicrobial activity of new piperine derivatives containing substituted δ-esters
Barbosa-Filho, José M.,Brandao, Maria C. R.,De Athayde-Filho, Petr?nio F.,Dutra, Thalisson F.,Lima, Edeltrudes O.,Lira, Bruno F.,Neto, Hermes Diniz,Trindade, Emmely O.
, p. 2590 - 2602 (2020/11/18)
A series of fifteen new piperine-derived diesters was synthesized through the substitution reaction between the salt of piperic acid, obtained through piperine basic hydrolysis, with the δ-chloro-esters, obtained through the cleavage of tetrahydrofuran (THF) with acyl chlorides in the presence of ZnCl2. The final compounds were obtained with yields ranging from 50 to 84% and were characterized by infrared (IR) and 1H and 13C nuclear magnetic resonance spectroscopy (NMR). The new compounds were evaluated in silico in regard to their ADME (absorption, distribution, metabolism, and excretion) properties, and in vitro for their antimicrobial activity against bacteria strains (Staphylococcus aureus and Pseudomonas aeruginosas), yeast fungi (Candida albicans and C. tropicalis) and filamentous fungi (Aspergillus fumigatus, A. flavus and A. niger). The results from the in silico studies of Lipinski's rule of five showed that most compounds present good pharmacological possibilities, and the results from in vitro antimicrobial activity showed that 8 of the 15 synthesized compounds displayed antimicrobial activity, inhibiting the growth of 40-80% of tested strains, with a minimum inhibitory concentration (MIC) interval ranging from 1024 to 256 μg mL-1
A Straightforward Conversion of Activated Amides and Haloalkanes into Esters under Transition-Metal-Free Cs 2 CO 3 /DMAP Conditions
Chen, Liuqing,Gu, Ying,Jian, Junsheng,Liu, Yueping,Miao, Liqiong,Wang, Zijia,Zeng, Zhuo
supporting information, p. 4078 - 4084 (2019/10/28)
The esterification of activated amides, N -acylsaccharins, under transition-metal-free conditions with good functional group tolerance has been developed, resulting in C-N cleavage leading to efficient synthesis of a variety of esters in moderate to good yields. This work demonstrates that esterification may proceed by using simple N -acylsaccharins, haloalkanes, and Cs 2 CO 3 as oxygen source.
Synthesis and characterization of 4-chlorobutyl ester of 5-(8-carboxyl-1-naphthyl)-10,15,20-triphenyl-porphyrin and its zinc complex
Liu, Huan,Ou, Caifen,Ma, Ben,Hu, Chuanjiang
, p. 597 - 602 (2017/08/10)
In the presence of Br?nsted–Lowry acids (phenol or dry HCl), the acyl chloride, which was obtained by the reaction between 5-(8-carboxyl-1-naphthyl)-10,15,20-triphenyl-porphyrin (CNTPP) and oxalyl chloride, reacted with tetrahydrofuran and led to the 4-chlorobutyl ester, P1, as the result of the acylative cleavage. P1 and its zinc complex [ZnP1] have been characterized by1H NMR. The structure of [ZnP1] was obtained by X-ray crystallography. Zinc is coordinated by four pyrrole nitrogens. The 8-position substituent, a 4- chlorobutyl ester group, lies above the porphyrin plane.
Palladium(II) acetate catalyzed acylative cleavage of cyclic and acyclic ethers under neat conditions
Fotie, Jean,Adolph, Brandy R.,Bhatt, Shreya V.,Grimm, Casey C.
supporting information, p. 4648 - 4651 (2017/11/15)
During the development of a palladium catalyzed C–H activation cross-coupling reaction involving acyl halides, it was noted that palladium(II) acetate catalyzes the acylative cleavage of tetrahydrofuran (used as a solvent) at room temperature to afford the corresponding 4-chlorobutyl ester derivative. After optimization, the reaction was shown to work well with epoxides, oxetane and tetrahydrofuran, but only barely with oxanes at room temperature. Acyclic ethers systematically failed to react under similar conditions, but underwent complete conversion in a microwave reactor at 100 °C.
Method for generating ester through reaction of benzoyl chloride and halogenated hydrocarbon
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Paragraph 0021; 0022; 0023, (2017/08/31)
The invention discloses a method for generating ester through reaction of benzoyl chloride and halogenated hydrocarbon. According to the method, benzoyl chloride, halogenated hydrocarbon and carbonate which are reaction substrates are heated and stirred to react in the presence of a catalyst 4-dimethylaminopyridine (DMAP) in an air or inert gas atmosphere to generate a corresponding ester product. The method disclosed by the invention has the beneficial effects that benzoyl chloride, halogenated hydrocarbon and carbonate are taken as the reaction substrates for the first time, carbonate is found as a source of oxygen in the product for the first time, and the reaction is found as a free radical mechanism for the first time.
Reaction of Acyl Chlorides with in Situ Formed Zinc Selenolates: Synthesis of Selenoesters versus Ring-Opening Reaction of Tetrahydrofuran
Bellino, Gemma,Scisciani, Marialaura,Vargas, Jaqueline Pinto,Sancineto, Luca,Bagnoli, Luana,Marini, Francesca,Lüdtke, Diogo Seibert,Lenardao, Eder Joao,Santi, Claudio
, (2016/07/28)
Attempting to apply the in situ production of PhSeZnSePh to the synthesis of selenoesters, an unexpected reaction involving the solvent (tetrahydrofuran) was observed and studied. We reported here some evidences about the mechanism and the possibility to
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.
