3395-80-0

Upstream product

• 67-56-1 methanol 
• 587-04-2 m-Chlorobenzaldehyde 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 1125-88-8 benzaldehyde dimethyl acetal 
• 90470-53-4 1-methoxy-1-(3-chlorophenyl)acetonitrile 
• 70097-44-8 7-chloro-3-hydroxyisobenzofuran-1(3H)-one 
• 865776-81-4 1-chloro-3-(1-methoxybut-3-enyl)benzene 
• 1240400-39-8 3-(3-chlorophenyl)-3-methoxy-1-phenylpropan-1-one 
• 90470-72-7 1,1-dimethoxy-1-(3-methylphenyl)methane 
• 100501-45-9 3-(dimethoxymethyl)benzaldehyde 
• 587-04-2 m-Chlorobenzaldehyde 
• 2972-73-8 2-(3-chlorobenzylidene)malononitrile 

Relevant academic research and scientific papers

Synthesis of DPA-triazole structures and their application as ligand for metal catalyzed organic reactions

In this work, the use of DPA-triazole (DPA = dipicolylamine) molecules as ligands for metal catalyzed organic reactions has been investigated. A small library of ligands has been prepared by a CuAAC (click reaction) between propargyl-DPA and different azi

Systematic Study of Regioselective Reductive Ring-Opening Reactions of 4,6- O-Halobenzylidene Acetals of Glucopyranosides

Reductive openings of cyclic acetals are widely used in modern synthetic organic chemistry for the regioselective introduction of protecting groups. A systematic study was performed on the applicability and efficacy of various hydride donor and protic or Lewis acid reagent combinations in the reductive ring opening of glucosidic 4,6-halobenzylidene acetals bearing an ortho-, meta-, and para-chloro- or -bromo substituent on the benzene ring. Most of the reagent combinations tested cleaved the 4,6-O-halobenzylidene acetal rings at O4 or O6 efficiently and with the expected regioselectivity. The LiAlH4-AlCl3 and the BH3·THF-TMSOTf combinations produced the 4-O-halobenzyl ether/6-OH products with complete regioselectivity and high yields. The use of Me3N·BH3-AlCl3 reagent system in toluene was also effective in cleaving the acetal ring at O6 but was accompanied by Al-chelation-assisted debenzylation side reactions. The NaCNBH3-HCl and the Et3SiH-BF3·Et2O combinations were highly effective in yielding the 6-halobenzyl ether/4-OH derivatives. Et3SiH, in combination with TfOH, produced the 6-O-ether/4-OH products in rapid reactions but also triggered silylation and reductive halobenzylation as secondary transformations. Reductive opening of the 1,3-dioxane ring of pyranosidic 4,6-O-halobenzylidene acetals by the proper reagent combination was found to be an efficient method for the regioselective introduction of versatile halobenzyl protecting groups onto the pyranose ring.

Synthesis, structural determination and catalytic study of a new 2-D chloro-substituted zinc phosphate, (C8N2H20)[ZnCl(PO3(OH))]2

A novel chloro-substituted zinc-phosphate, (C8N2H20)[ZnCl(PO3(OH))], has been synthesized by a slow evaporation method in the presence of 1,3-cyclohexanebis- (methylamine), which acts as a template. The structure consists of vertex linked ZnO3Cl and PO3(OH) tetrahedral, assembled into corrugated porous layers [ZnCl(PO3(OH))2]∞ with (4.82) topology. The optical properties were also investigated using Diffuse Reflecting Spectroscopy (DRS), showing that the title compound has semiconducting properties. In addition, the catalytic activity of (C8N2H20)[ZnCl(PO3(OH))]2 has been tested in the acetalisation reaction of aldehydes. The title compound displayed a high catalytic activity with practically total conversion in many examples using MeOD as solvent and as the sole source of acetalisation. More importantly, the reaction crudes are very clean and only the preferred products are found in the NMR spectra.

Nickel-Catalyzed Chemoselective Acetalization of Aldehydes With Alcohols under Neutral Conditions

A molecularly defined NiII-complex catalyzing the chemoselective acetalization of aldehydes with alcohols under neutral conditions is reported. The reaction is general, efficient and showed a wide substrate scope (including aliphatic aldehydes) as well as excellent functional group tolerance. Reusability of the present nickel catalyst is also demonstrated.

House bulb light-induced photochemical acetalization of carbonyl compounds catalyzed by Eosin Y

We have systematically studied the reactions of acetalization and found that high reaction efficiency can be achieved using cheap and readily available organic Eosin Y as catalyst. The reaction proceeds smoothly under house bulbs and shows excellent functional group tolerance. The substrates of the reaction system are compatible with aromatic aldehydes, aliphatic aldehydes, aromatic ketones, and cyclic ketones with high yields.

Hydrothermal synthesis of chiral inorganic-organic CoII complex: Structural, thermal and catalytic evaluation

By heating the cobalt chloride hexahydrate (CoCl2·6H2O) with the R form of the organic amine α-methylbenzylamine (C8H11N) under hydro(solvo)thermal conditions, we have successfully generated the corresponding non-centrosymmetric homochiral hybrid tris (α-methylbenzylammonium tetrachloridocobaltate chloride [R-(C8H12N)3][CoCl4]Cl abbreviated R(MBA)Co. We present the growth conditions together with a characterization of the single crystals by means of X-ray single-crystal diffraction, Fourier-transform infrared, TG/TDA thermal decomposition and catalytic properties. This inorganic–organic hybrid compound crystallizes in the chiral space group P21 and exhibits a supramolecular-layered organization wherein a double layer of (R)-methylbenzylammonium cations and the uncoordinated chloride anions are sandwiched between anionic layers, formed by isolated tetrachloridocobaltate tetrahedra. The crystal packing is governed by a three-dimensional network of N/C–H?Cl hydrogen bonds between the inorganic and organic moieties and C–H···π interactions between the aromatic rings of the organic moieties themselves. Thermal analysis discloses a phase transition at the temperature 130 °C. The Co complex was also employed as suitable catalyst activating the acetal formation reaction of aldehydes using MeOH as solvent and as the unique source of acetalization.

Silver-Catalyzed Olefination of Acetals and Ketals with Diazoesters to β-Alkoxyacrylates

The first silver-catalyzed reaction of acetals or ketals with diazoesters leading to trisubstituted or tetrasubstituted β-alkoxyacrylates is now reported. A broad range of acetals and ketals bearing different substituents is compatible with this protocol and thus provides an attractive approach for the synthesis of complex β-alkoxyacrylates. The power of this method was further demonstrated by the successful synthesis of picoxystrobin, which is one of the most popular agricultural fungicides commercialized by Dupont.

Acid-catalyzed highly diastereoselective and effective synthesis of 1,3-disubstituted tetrahydropyrano[3,4-b]indoles

We successfully explored for the first time that trifluoroacetic acid (TFA) can effectively catalyze the oxa-Pictet-Spengler reaction of secondary tryptophols and acetals to synthesize 1,3-disubstituted 1,3,4,9-tetrahydropyrano[3,4-b]indoles in high yield (up to >99%) and diastereoselectivity (>20:1). The secondary tryptophols were synthesized from indole-3-acetic acid. The one-pot synthesis of tetrahydropyrano[3,4-b]indoles was successfully developed from secondary tryptophols and in situ prepared acetals from aldehydes and trimethylorthoformate and thus the cost-efficiency of the protocol was effectively enhanced. Finally, the catalytic asymmetric synthesis of the 1,3-disubstituted tetrahydropyrano[3,4-b]indole was also demonstrated after enantioselective achievement of highly enantiopure secondary tryptophols.

Crystallisation, thermal analysis and acetal protection activity of new layered Zn(II) hybrid polymorphs

Two new polymorphic mononuclear complexes, with analogous structural formula (C6H9N2)2[Zn(H2O)6](SO4)2·2H2O, of zinc(ii) templated by 2-amino-6-methylpyridinium ligand have been discovered. These polymorphic hybrid crystals, which differ only in terms of their crystal structures, were prepared in one-step synthesis under ambient conditions and investigated for their thermal and catalytic properties. Single-crystal X-ray diffraction of the obtained materials revealed that polymorphs 1 and 2 crystallise in the triclinic system, space group P1. In an effort to further explore the form diversity of these compounds, the structural arrangements and intermolecular interactions such as hydrogen-bonding and π?π interactions are discussed from which supramolecular assembly was formed. Meanwhile, these new polymorphic forms can be described as the stacking of 3D layers where the interlayer distances are 13.23 and 12.59 ? for 1 and 2, respectively. The thermal behaviour of the precursors checked by TG-DTA analysis for both zinc sulfate polymorphs and variable temperature powder X-ray diffraction (VT-PXRD) show successive intermediate crystalline anhydrous phases upon dehydration in 1. The catalytic activity of both polymorphic structures has been tested in the acetalisation reaction of aldehydes as a benchmark process. Interestingly, both complexes showed excellent activity with almost total conversion in many examples and using MeOH as solvent and as the unique source of acetalisation.

A new generation of aprotic yet Bronsted acidic imidazolium salts: Low toxicity, high recyclability and greatly improved activity

Catalysts which have low antimicrobial toxicity and are aprotic, yet which can act as Bronsted acidic catalysts in the presence of protic additives have been developed. The catalysts are recyclable, considerably more active (i.e. can be used at 10-50 times lower loadings) and of broader scope than their antecedent generation.