66822-17-1Relevant academic research and scientific papers
Synthesis method of substituted benzaldehyde acetal
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Paragraph 0073-0076; 0084-0090; 0130-0157, (2022/03/31)
The invention provides a synthetic method of substituted benzaldehyde acetal. The substituted benzaldehyde acetal has a structure as shown in a formula (I), wherein X1 and X2 are respectively independently selected from halogen or vacancy, and n is 1 or 2; the synthesis method comprises the following steps: in an inert gas atmosphere, carrying out a reduction reaction on substituted nitrobenzene in the presence of a nickel catalyst to obtain substituted aniline, and carrying out the reduction reaction in a first solvent: in a second solvent, carrying out an oxidation denitrification rearrangement reaction on the substituted aniline, paraformaldehyde and an oxidizing agent to obtain substituted benzaldoxime; substituted benzaldoxime, hydroquinone and dihydric alcohol are subjected to an aldehyde group protection reaction in the presence of a solid acid catalyst to obtain substituted benzaldehyde acetal, wherein the solid acid catalyst is a solid superacid compound. The substituted benzaldehyde acetal prepared by the method has high yield and purity, the reaction raw materials are simple and easy to obtain, the reaction conditions are mild, the cost is low, and large-scale production is facilitated.
Application of poly(Vinylbenzyltrimethylammonium tribromide) resin as an efficient polymeric catalyst in the acetalization and diacetylation of benzaldehydes
Han, Bingbing,Hu, Junjun,Li, Xianwei,Zheng, Zubiao
supporting information, p. 287 - 293 (2021/04/28)
The applications of a new supported tribromide reagent (poly(vinylbenzyltrimethylammonium tribromide) resin) were reported. This supported tribromide resin was used as a catalyst in the acetalization and diacetylation of benzaldehydes under mild conditions with high efficiency. The effects of solvents, and amount of the supported tribromide resin on the reactions were investigated. Under the optimal conditions, most of acetal and 1,1-diacetates of benzaldehydes were selectively obtained in excellent yields.
Photocatalytic Reductive Formation of α-Tertiary Ethers from Ketals
Rossolini, Thomas,Ferko, Branislav,Dixon, Darren J.
supporting information, p. 6668 - 6673 (2019/09/03)
A general photocatalytic reductive strategy for the construction of unsymmetrical α-tertiary dialkyl ethers is reported. By merging Lewis acid-mediated ketal activation and visible-light photocatalytic reduction, in situ-generated α-alkoxy radicals were found to engage in addition reactions with a variety of olefinic partners. Good reaction efficiency is demonstrated with a range of ketals of aromatic and aliphatic ketones. Extension to acetal substrates is also described, demonstrating the overall synthetic utility of this methodology for complex ether synthesis.
The Hydrazine–O2 Redox Couple as a Platform for Organocatalytic Oxidation: Benzo[c]cinnoline-Catalyzed Oxidation of Alkyl Halides to Aldehydes
Stone, Ilana B.,Jermaks, Janis,MacMillan, Samantha N.,Lambert, Tristan H.
supporting information, p. 12494 - 12498 (2018/09/18)
An organocatalytic oxidation platform that capitalizes on the capacity of hydrazines to undergo rapid autoxidation to diazenes is described. Commercially available benzo[c]cinnoline is shown to catalyze the oxidation of alkyl halides to aldehydes in a novel mechanistic paradigm involving nucleophilic attack, prototropic shift, and hydrolysis. The hydrolysis and reoxidation events occur readily with only adventitious oxygen and water. A survey of the scope of viable substrates is shown along with mechanistic and computational studies that give insight into this mode of catalysis.
Visible-light-induced acetalization of aldehydes with alcohols
Yi, Hong,Niu, Linbin,Wang, Shengchun,Liu, Tianyi,Singh, Atul K.,Lei, Aiwen
supporting information, p. 122 - 125 (2017/11/27)
In this work, we have achieved a simple and general method for acetalization of aldehydes by means of a photochemical reaction under low-energy visible light irradiation. A broad range of aromatic, heteroaromatic, and aliphatic aldehydes have been protected under neutral conditions in good to excellent yields using a catalytic amount of Eosin Y as the photocatalyst. Our visible light mediated acetalization strategies are successful for more challenging acid-sensitive aldehydes and sterically hindered aldehydes. Notably, this protocol is chemoselective to aldehydes, while ketones remain intact.
Synthesis and characterization of a tetracationic acidic organic salt and its application in the synthesis of bis(indolyl)methanes and protection of carbonyl compounds
Halimehjani, Azim Ziyaei,Hooshmand, Seyyed Emad,Shamiri, Elham Vali
, p. 21772 - 21777 (2015/03/18)
A new tetracationic acidic organic salt (TCAOS) based on DABCO was prepared, characterized and applied as an eco-friendly, powerful and reusable catalyst for the synthesis of bis(indolyl)methanes from indoles and carbonyl compounds in water with high turnover frequency (TOF). Also, this catalyst was successfully applied for acetalization of carbonyl compounds with diols under solvent-free conditions.
Tandem catalysis by palladium nanoclusters encapsulated in metal-organic frameworks
Li, Xinle,Guo, Zhiyong,Xiao, Chaoxian,Goh, Tian Wei,Tesfagaber, Daniel,Huang, Wenyu
, p. 3490 - 3497 (2015/02/19)
A bifunctional Zr-MOF catalyst containing palladium nanoclusters (NCs) has been developed. The formation of Pd NCs was confirmed by transmission electron microscopy (TEM) and extended X-ray absorption fine structure (EXAFS). Combining the oxidation activity of Pd NCs and the acetalization activity of the Lewis acid sites in UiO-66-NH2, this catalyst (Pd@UiO-66-NH2) exhibits excellent catalytic activity and selectivity in a one-pot tandem oxidation-acetalization reaction. This catalyst shows 99.9% selectivity to benzaldehyde ethylene acetal in the tandem reaction of benzyl alcohol and ethylene glycol at 99.9% conversion of benzyl alcohol. We also examined various substituted benzyl alcohols and found that alcohols with electron-donating groups showed better conversion and selectivity compared to those with electron-withdrawing groups. We further proved that there was no leaching of active catalytic species during the reaction and the catalyst can be recycled at least five times without significant deactivation.
Homologative trifluoromethylation of acetals
Hamilton, James Y.,Morandi, Bill,Carreira, Erick M.
, p. 1857 - 1862 (2013/07/26)
Trifluoroethyl α-insertion of acetals has been developed. Aromatic, heteroaromatic, and alkenyl acetals react with in situ generated (trifluoromethyl)diazomethane in the presence of antimony(V) chloride to furnish α-trifluoromethyl acetals. A stereoselective version of this transformation exploiting the acetal as a chiral auxiliary is also presented. Georg Thieme Verlag Stuttgart · New York.
Triazole Compounds, Use Thereof and Agents Containing Same
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Page/Page column 46, (2011/08/02)
The present invention relates to compounds of the formula I in which the variables have the meanings defined in the claims and in the description.
Highly efficient and chemoselective acetalization of carbonyl compounds catalyzed by new and reusab e zirconyl triflate, zr0(0tf)2
Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Tangestaninejad, Shahram,Mirkhani, Valiollah,Yazdani, Parvin,Ghorjipoor, Saeedeh
experimental part, p. 131 - 135 (2009/09/30)
Various types of aromatic aldehydes were efficiently converted to their corresponding 1,3-dioxanes and 1,3-dioxolane with 1,3-propanediol and ethylene glycol, respectively, in the presence of catalytic amount of ZrO(OTf) 2 in acetonitrile at room temperature. The catalyst can be reused several times without loss of its catalytic activity. Very short reaction times, selective acetalization of aromatic aldehydes in the presence of aliphatic aldehydes and ketones, very mild reaction conditions, reusability of the catalyst, and easy workup are noteworthy advantages of this method.
