13540-50-6

Usage

Synthesis Reference(s)

Tetrahedron Letters, 32, p. 1423, 1991 DOI: 10.1016/0040-4039(91)80347-9

InChI:InChI=1/C15H16/c1-12-8-9-13(2)15(10-12)11-14-6-4-3-5-7-14/h3-10H,11H2,1-2H3

Upstream product

• 4044-60-4 2,5-dimethylbenzophenone 
• 106-42-3 para-xylene 
• 100-44-7 benzyl chloride 
• 100-51-6 benzyl alcohol 
• 104-57-4 benzyl formate 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 115975-28-5 benzyl α-bromo-o-toluate 
• 100-39-0 benzyl bromide 
• 108-88-3 toluene 
• 71-43-2 benzene 
• 28867-76-7 benzaldehyde benzylidenehydrazone 
• 100-52-7 benzaldehyde 
• 772-01-0 2-phenyl-1,3-dioxane 
• 7664-93-9 sulfuric acid 

Downstream Products

• 613-12-7 2-methylanthracene 
• 573-69-3 benzophenone-2,5-dicarboxylic acid 
• 4044-60-4 2,5-dimethylbenzophenone 
• 86846-64-2 (2,5-Dimethyldiphenylmethyl)lithium 
• 25401-28-9 (4-Benzyl-2,5-dimethyl-phenyl)-(4-chloro-phenyl)-methanone 
• 85914-51-8 2,5-dimethyl-4-chloromethyldiphenylmethane 
• 1514862-82-8 4-benzyl-4'-fluoro-2,5-dimethyl-1,1'-biphenyl 
• 25420-67-1 2-Benzoyl-5-(4-chloro-benzoyl)-terephthalic acid 
• 25401-26-7 2-Benzoyl-5-(2-chloro-benzoyl)-terephthalic acid 
• 106147-67-5 4-[2-(2,5-Dimethyl-phenyl)-2-phenyl-ethyl]-1H-imidazole 
• 34835-71-7 2,4,5-trimethyldiphenylmethane 
• 25401-25-6 (4-Benzyl-2,5-dimethyl-phenyl)-(2-chloro-phenyl)-methanone 

Relevant academic research and scientific papers

The catalytic Friedel-Crafts alkylation reaction of aromatic compounds with benzyl or allyl silyl ethers using Cl2Si(OTf)2 or Hf(OTf)4

The Friedel-Crafts alkylation reaction of various aromatic compounds with benzyl or allyl silyl ethers is effectively promoted under mild reaction conditions using Lewis acid catalysts. A mixture of the desired phenyltolylmethanes is obtained in 80% yield from toluene with benzyl dimethylsilyl or trimethylsilyl ether at 50°C in the presence of a catalytic amount of Cl2Si(OTf)2 or Hf(OTf)4.

Helical Al- and Ce-MCM-41 materials as novel catalyst for acid and redox processes

Helical mesoporous silicas containing aluminium or cerium into their framework have been synthesized via hydrothermal method. The synthesized materials were extensively characterized to understand their physico-chemical properties in view of their future catalytic applications. Low-angle powder XRD patterns of calcined samples showed a hexagonally ordered mesopore structure. NMR spectra of aluminium materials exhibited two signals at 50 and 0 ppm assigned to tetracoordinated and octahedrally coordinated Al3+. DR-UV-vis and XPS spectrum of cerium content materials show that cerium was incorporated as Ce3+ and Ce4+ into the helical mesoporous material. Materials with molar ratios Si/Al = 95 and Si/Ce = 500 were found to be catalytically active in acid (oxathioacetalisations and alkylations) or redox (epoxidation of cyclohexene) catalyzed processes, respectively.

Dihalogen-halogenomethyl complexes of indium(III) X2InCH2X (X = Br, I): Simultaneous coordination of soft and hard ligands

Halogenomethyl-dihalogen-indium(III) compounds X2InCH2X (X = Br, I) obtained from indium monohalides and methylene dihalides were reacted with the soft donor ligands dialkylsulfides, R2S (R = CH3, CH2

Multifunctional oxygen vacancies in WO3–x for catalytic alkylation of C–H by alcohols under red-light

Surface reaction kinetics and light absorption properties of a photocatalyst are essential demands for efficiently solar to chemical energy converting. In this study, plasmonic WO3–x was firstly applied to photocatalytic alkylation of arenes under red light irradiation. The oxygen vacancies, both on the surface and in the bulk of WO3–x, allow abundant free electrons to increase carrier densities and support its LSPR using low energy photons. The surface oxygen vacancies have more functions: they not only release surface tungsten sites which ensure the chemisorption of alcohols due to the coordianation ability but also promote the activation of alcohols via an efficient transport of the holes on the neighbouring O sites to chemisorption alcohol species. In brief, the bulk oxygen vacancies provide abundant charges and the surface vacancies promote the bond adsorption and activation abilities, which ensure the high efficiency of photocatalytic alkylation of C–H.

Development of highly efficient Friedel-Crafts alkylations with alcohols using heterogeneous catalysts under continuous-flow conditions

The development of Friedel-Crafts alkylations with alcohols under continuous-flow conditions using heterogeneous catalysts is reported. The reactivities and durabilities of the examined catalysts were systematically investigated, which showed that montmorillonite clay is the best catalyst for these reactions. A high turnover frequency of 9.0 × 102h?1was recorded under continuous-flow conditions, and the continuous operation was successfully maintained over one week.

Friedel–Crafts benzylation of toluene catalyzed by ZnCl2/SiO2 heterogeneous catalyst to para- and ortho-mono-benzylated toluene

A series of catalysts was prepared for the liquid-phase Friedel–Crafts benzylation of toluene with benzyl chloride (BC) by impregnating rice husk ash silica with ZnCl2 (3?wt%, 6?wt%, 9?wt%, and 12?wt%) via a wet impregnation method. The XRD analysis indicates that the catalysts were amorphous with ill-defined pore systems. The XPS analysis detected the coexistence of ZnO nanoparticles together with ZnCl2 on the catalyst surface, whereas the 29Si NMR analysis indicates the formation of Si–O–Zn bond. Quantitative conversion of benzyl chloride (100%) was achieved within 3?h at 353?K when a catalyst with 9?wt% ZnCl2 was used due to its narrow pore size and high surface area (635?m2?g?1). Para- and ortho-mono-benzylated toluene was obtained as the products. The reaction is proposed to take place via weak attraction between benzyl chloride and the Zn through its chlorine atom. The catalyst was recycled four times with minimum loss (8%) in activity. The benzylation of benzene, toluene, p-xylene, and anisole followed the classical mechanism of Friedel–Craft-type acid-catalyzed benzylation reaction. The BC conversion increased in the order of toluene = p-xylene > anisole > benzene. The catalyst was also screened to be active in the benzoylation of toluene with benzoyl chloride (BOC). The conversion of BOC was 45% with selectivity toward 2-methylbenzophenone (50%) and 3-methylbenzophenone (50%).

Selective Conversion of Benzylic Phosphates into Diarylmethanes Through Al(OTf)3-Catalyzed Friedel–Crafts-Type Benzylation

Al(OTf)3 was identified as a high-performance catalyst for Friedel–Crafts-type benzylation using benzylic phosphates as electrophiles. The reaction proceeded even with 0.2 mol-% of the catalyst. A series of diarylmethanes (21 examples) was obtained in moderate to high yield. The catalyst showed unique chemoselectivity, preferentially converting the benzylic phosphate motif, even with a benzylic acetate group existed in the same molecule.

Benzylation of Arenes with Benzyl Halides under Promoter-Free and Additive-Free Conditions

It was found that benzyl chlorides and bromides could directly react with electron-rich arenes, which provided an example of promoter-free and additive-free benzylation of arenes. A variety of benzyl chlorides and bromides were treated with benzene rings to give the targeted products in low to high yields. The present conditions tolerated the vinyl group of the substrates. Preliminary mechanistic investigation suggests that the present reactions possibly proceed via an autocatalytic mechanism pathway.

Catalytic arene alkylation over H-Beta zeolite: Influence of zeolite shape selectivity and reactant nucleophilicity

Renewable arenes and aromatic alcohols can be derived from lignocellulose by biorefineries, which has been considered as a sustainable alternative to replace petrochemical feedstocks in the synthesis of monobenzylation products, key industrial intermediates, via benzylation reactions. Zeolites with micropores are the most widely used catalysts in the benzylation of arenes, however, their performance suffers from diffusion limitations in converting large arenes. In this work, mesoporous and microporous H–Beta zeolites were prepared and applied in the systematic study of benzylation of arenes (benzene, toluene, p-xylene and mesitylene) with benzyl alcohol (BA). The porous structure of these zeolites has been confirmed by XRD, BET and TEM techniques. The catalytically active Br?nsted acid sites (BAS) were determined by quantitative 1H magic-angle spinning (MAS) nuclear magnetic resonance (NMR) experiments. The benzylation studies have shown that introducing mesopores into H–Beta zeolites can significantly increase the diffusion/access of arenes to surface sites, particularly for bulky arenes (e.g. mesitylene), while micropores are mainly selective for the conversion of small arenes (e.g. benzene). Increasing the nucleophilicity of arenes with more alkyl groups can enhance their catalytic performance in mesopores, however, the increase hinders their conversion in micropores because of the shape selectivity due to their increasing molecular size. Compared to mesopores, micropores promote the conversion of small arenes (e.g. benzene), which can be additionally enhanced by a high Br?nsted acidity. Therefore, introducing a suitable porosity balanced with acidity are keys in the tailoring of the catalytic performance of H-Beta zeolites for target benzylation reactions.

Bisulfate Salt-Catalyzed Friedel-Crafts Benzylation of Arenes with Benzylic Alcohols

We report here a method of direct Friedel-Crafts benzylation of arenes with benzylic alcohols using cheap and readily available bisulfate salt as the catalyst in hexafluoroisopropanol. The catalytic system is powerful with a quite diverse group of functionalized arenes and benzylic alcohols. These mild conditions provide a straightforward synthesis of a variety of unsymmetrical diarylmethanes in high yield with good to high regioselectivity. An SN1 mechanism involving activation of the hydroxy group through a hydrogen bond is proposed.