- Efficient selective synthesis of ethylbenzonitriles
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Ethylbenzonitriles were synthesized by selective gas-phase ammoxidation of ethylbenzyl chlorides prepared by chloromethylation of ethylbenzene in good yields and almost 100% selectivity at ca. 200 °C for the first time.Copyright Taylor & Francis Group, LLC.
- Xie, Guangyong,Zhang, Aiqing
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Read Online
- Cu(II)/Cu(0)@UiO-66-NH2: Base metal@MOFs as heterogeneous catalysts for olefin oxidation and reduction
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Two copper-loaded MOF materials, namely Cu(ii)@Ui-O-66-NH2 (1) and Cu(0)@UiO-66-NH2 (2), are reported. They can, respectively, serve as highly efficient heterogeneous catalysts for olefin oxidation and hydrogenation under mild conditions. Complete styrene hydrogenation occurs in 15 min at ambient temperature with quantitative yield.
- Wang, Jian-Cheng,Hu, Yu-Hong,Chen, Gong-Jun,Dong, Yu-Bin
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Read Online
- Structure-guided optimization of 1H-imidazole-2-carboxylic acid derivatives affording potent VIM-Type metallo-β-lactamase inhibitors
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Production of metallo-β-lactamases (MBLs) in bacterial pathogens is an important cause of resistance to the ‘last-resort’ carbapenem antibiotics. Development of effective MBL inhibitors to reverse carbapenem resistance in Gram-negative bacteria is still needed. We herein report X-ray structure-guided optimization of 1H-imidazole-2-carboxylic acid (ICA) derivatives by considering how to engage with the active-site flexible loops and improve penetration into Gram-negative bacteria. Structure-activity relationship studies revealed the importance of appropriate substituents at ICA 1-position to achieve potent inhibition to class B1 MBLs, particularly the Verona Integron-encoded MBLs (VIMs), mainly by involving ingenious interactions with the flexible active site loops as observed by crystallographic analyses. Of the tested ICA inhibitors, 55 displayed potent synergistic antibacterial activity with meropenem against engineered Escherichia coli strains and even intractable clinically isolated Pseudomonas aeruginosa producing VIM-2 MBL. The morphologic and internal structural changes of bacterial cells after treatment further demonstrated that 55 crossed the outer membrane and reversed the activity of meropenem. Moreover, 55 showed good pharmacokinetic and safety profile in vivo, which could be a potential candidate for combating VIM-mediated Gram-negative carbapenem resistance.
- Yan, Yu-Hang,Li, Wenfang,Chen, Wei,Li, Chao,Zhu, Kai-Rong,Deng, Ji,Dai, Qing-Qing,Yang, Ling-Ling,Wang, Zhenling,Li, Guo-Bo
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- Preparation method of 4-ethylbenzyl chloride
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The invention discloses a preparation method of 4-ethylbenzyl chloride, and belongs to the technical field of organic synthesis. The method comprises the following steps: chloromethylating ethylbenzene serving as a raw material with acetal, chlorosulfonic acid and lewis acid under the catalytic action to obtain 4-ethylbenzyl chloride. According to the method, the catalyst can be recycled and reused, isomers are few, separation is relatively easier, the yield is high, the content of the obtained product is larger than 99%, and potential industrial amplification prospects are achieved.
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Paragraph 0027-0029
(2021/11/26)
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- An efficient and convenient chloromethylation of some aromatic compounds catalyzed by zinc iodide
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Treatment of a series of aromatic hydrocarbons and O-carbethoxy phenol substrates with a mixture of chlorosulfonic acid and dimethoxymethane in CH2Cl2 catalyzed by zinc iodide affords the corresponding chloromethyl derivatives in good to excellent yields.
- Tang, Jian,Liu, Hongtao,Zhou, Jing,Zhang, Xingxian
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- A practical and convenient Blanc-type chloromethylation catalyzed by zinc chloride under solvent-free conditions
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Chloromethylation of various aromatic hydrocarbons and substituted phenolic derivatives with dimethoxymethane and chlorosulfonic acid was carried out in the presence of 10 mol% of ZnCl2 in a mild and efficient manner under solvent-free conditions. In addition, 2,6-dimethyltyrosine was synthesized in high yield via this protocol.
- Tang, Jian,Liu, Hongtao,He, Kailun,Zhang, Xingxian
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p. 925 - 932
(2019/03/17)
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- A method of preparing intermediates sea breeze aldehyde
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The invention discloses a method of preparing a floralozone intermediate. Under the action of an aqueous sulfuric acid solution and a quaternary ammonium salt as a phase transfer catalyst, by controlling the reaction temperature, hydrogen chloride gas is continuously fed into a reaction system containing ethylbenzene and paraformaldehyde so as to perform chloromethylation of the ethylbenzene, and ethylbenzyl chloride with a purity higher than 95% and a yield being 85-94% is finally prepared. By adoption the ethylbenzyl chloride as the intermediate, floralozone can be prepared by condensing the intermediate and isobutyraldehyde.
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Paragraph 0056-0060
(2017/02/09)
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- A method of preparing sea breeze aldehyde
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The invention discloses a preparation method of floralozone. The preparation method comprises the steps of dropwise adding isobutyraldehyde into an ethyl benzyl chloride contained reaction system through controlling the reaction temperature under the action that sodium hydroxide and quaternary ammonium salt compounds are used as phase transfer catalysts, and finally, preparing at the yield of 70-85% to obtain floralozone with the content up to more than 94%. The preparation method of floralozone, disclosed by the invention, is low in yield of three wastes, strong in process operability and low in cost.
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Paragraph 0088-0092
(2017/02/23)
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- An inexpensive and convenient procedure for chloromethylation of aromatic hydrocarbons by phase transfer catalysis in aqueous media
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Reaction of aromatic hydrocarbons catalyzed by a novel catalytic system consisting of zinc chloride, acetic acid, sulfuric acid and PEG-800 in aqueous media under PTC conditions results in chloromethylation in good to excellent yield.
- Hu, Yu Lin,Lu, Ming,Ge, Qiang,Wang, Peng Cheng,Zhang, Sheng Bin,Lu, Ting Ting
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experimental part
p. 97 - 102
(2010/08/05)
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- BENZODIAZEPINONE COMPOUNDS USEFUL IN THE TREATMENT OF SKIN CONDITIONS
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The present invention provides a family of benzodiazepinone compounds and pharmaceutical compositions thereof. The present invention also provides methods of treating certain skin conditions, e.g., atopic dermatitis, rosacea, or psoriasis, by administering a benzodiazepinone and methods of reducing the proliferation of keratinocyte cells by exposing such cells to a benzodiazepinone.
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Page/Page column 17
(2009/05/28)
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- Enhanced Pd-catalyzed hydrogenation of olefins within polymeric microreactors under organic/aqueous biphasic conditions
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A microreactor of a water-soluble hollow polymeric microsphere with Pd nanoparticles immobilized in the wall was proposed for the hydrogenation of olefins under organic and aqueous biphasic conditions. It was found that the microreactor was stable and was used in practical application for continuous hydrogenation of olefins on a technical scale without deactivation in activity. It was composed of three parts, such as the outer corona of polyacrylamide (PAM), the cross-linked and hydrophobic wall of poly[styrene-co-2-(acetoacetoxy) -ethylmethacrylate] (PS-co-PAEMA), and 3.9 mm Pd nanoparticles. Hollow microspheres were constructed using several procedures of seed polymerization along with removal of the seed for the synthesis of the microreactor. It was observed that the microreactor dispersed easily in aqueous phase due to the presence of the hydrophilic PAM corona. The hydrogenation of CA with H 2 was also evaluated to investigate hydrogenation of olefins within the microreactor.
- Lan, Yang,Zhang, Minchao,Zhang, Wangqing,Yang, Li
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scheme or table
p. 3670 - 3673
(2009/12/05)
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- Identification of alkylarene chloromethylation products using gas-chromatographic retention indices
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Gas-chromatographic retention indices on standard nonpolar polydimethylsiloxane stationary phases allow identification of products formed by known organic reactions even without using mass-spectrometric data. The efficiency of this approach was demonstrated by the example of identification of previously uncharacterized chloromethyl derivatives of alkylarenes, including structural isomers of compounds containing several chloromethyl groups, directly in reaction mixtures. Chromatographic analysis of such reaction mixtures allows identification of positional isomers of the starting alkylarenes even when they are present simultaneously. The retention indices were determined for the first time for more than 50 alkyl-(chloromethyl)arenes, by-products of chloromethylation, and chloromethyl derivatives of the simplest alkyl phenyl ketones. Nauka/Interperiodica 2007.
- Zenkevich,Makarov
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p. 611 - 619
(2008/03/18)
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- Reactions in Microemulsion Media. Nucleophilic Substitution Reactions of Benzyl and p-Alkylbenzyl Chlorides
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A kinetic and synthetic study of nucleophilic displacement reaction of bromide ion with benzyl chloride (1a) and its p-ethyl-substituted (1b) and p-n-dodecyl-substituted (1c) analogues has been performed in microemulsions prepared from combinations of a 1.23:1 (w/w) mixture (S) of cetyltrimethylammonium bromide (CTABr) and 1-butanol, a 1:5 (w/w) KBr-H2O solution (W), and hexane (O).The rates of reaction decreased differentially with increasing hexane content at a constant ratio of S:W to indicate that the interphase was the microemulsion reactive site.For microemulsion with respect to aqueous micellar and aqueous ethanol reaction media, solubilization of substrate was higher, initial reaction rates were comparable or slightly less, and overall conversions were greater.
- Martin, Craig A.,McCrann, Patrick M.,Ward, Mary Darlene,Angelos, George H.,Jaeger, David A.
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p. 4392 - 4396
(2007/10/02)
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- ipso Nitration. XXIII. Reactions of cyclohexadiene adducts from nitration of 4-ethyltoluene in acetic anhydride
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The diastereoisomers of 4-ethyl-1-methyl-4-nitrocyclohexa-2,5-dienyl acetate (1) and 1-ethyl-4-methyl-4-nitrocyclohexa-2,5-dienyl acetate (2) are stereospecifically reduced to the corresponding nitrocyclohexadienols with aluminum hydride.Each dienol is stereospecifically methylated to the corresponding methyl ether with methyl iodide, silver oxide, and potassium hydroxide.Acid-catalysed solvolysis of the acetates 1 and 2 results in the substitution of the acetate moiety by other nucleophiles and these reactions are not stereospecific.The products of rearomatization of dienyl acetates, dienols and dienyl methyl ethers depend on the acidity and ionizing power of the solvents and are readily explained in terms of reactions involving a nitrocyclohexadienyl cation or acetoxy- (hydroxy-, methoxy-)cyclohexadienyl cation as key intermediates.In the 4-acetoxy-4-alkylcyclohexadienyl cation 1,2-migration of the acetoxyl group is more rapid then alkyl migration, but 1,2-alkyl migration is faster then migration of the hydroxyl or methoxyl groups in the corresponding cations. 1-Ethyl-4-methoxy-4-methylcyclohexa-2,5-dien-1-ol and 4-ethyl-3-nitrotoluene are significant minor products in the solvolysis of 1-ethyl-4-methyl-4-nitrocyclohexa-2,5-dien-1-ol in aqueous methanol.Nitration of p-ethyltoluene in the presence of sulfuric acid or in trifluoracetic anhydride gives a mixture of 4-ethyl-2-nitro- and 4-ethyl-3-nitrotoluene in a 2:1 ratio.
- Fischer, Alfred,Henderson, George N.
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p. 2314 - 2327
(2007/10/02)
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