52458-10-3

Upstream product

• 98-54-4 para-tert-butylphenol 
• 108-88-3 toluene 
• 260783-80-0 N,N,N--trimethyl--1--phenylmethanaminium trifluoromethanesulfonate 
• 100-39-0 benzyl bromide 
• 253185-03-4 tert-butylbenzene 
• 84563-54-2 bis(4-tert-butylphenyl)iodonium trifluoromethanesulfonate 
• 100-51-6 benzyl alcohol 
• 28528-33-8 4-t-butylphenolate anion 
• 100-44-7 benzyl chloride 

Downstream Products

• 61516-22-1 2-benzyl-4-(tert-butyl)phenol 
• 22543-74-4 4-tert-butylbenzhydrol 
• 1448792-76-4 3-benzyl-5-(tert-butyl)-2-hydroxybenzaldehyde 
• 52458-13-6 4-tert-Butyl-benzhydryl-phenyl-keton 
• 98-54-4 para-tert-butylphenol 
• 52458-11-4 1-benzyloxy-2-bromo-4-tert-butylbenzene 
• 135505-54-3 N-<4-(1,1-Dimethylethyl)phenyl>-N-phenyl-1-naphthalenemethanamine 

Relevant academic research and scientific papers

Method for synthesizing aryl benzyl ether compound

The invention discloses a method for synthesizing aryl benzyl ether compounds, which comprises the following steps: by using an iron (III) complex containing 1, 3-di-tert-butyl imidazole cations and having a molecular formula of [(tBuNCH = CHNtBu) CH] [FeBr4] as a catalyst and di-tert-butyl peroxide as an oxidant, carrying out oxidative coupling reaction on phenolic compounds and toluene compounds to synthesize the corresponding aryl benzyl ether compounds. The method is the first example for preparing the aryl benzyl ether compound through the oxidative coupling reaction of the phenolic compound and the toluene compound, which is realized by an iron-based catalyst, and has the advantages of atom economy, environmental friendliness and good substrate applicability.

Application of iron (III) complex containing 1,3-di-tert-butyl imidazole cations in synthesis of aryl benzyl ether compounds

The invention discloses an application of an iron (III) complex containing 1,3-di-tert-butyl imidazole cations in synthesis of aryl benzyl ether compounds, and particularly relates to a method for synthesizing corresponding aryl benzyl ether compounds by taking di-tert-butyl peroxide as an oxidizing agent and carrying out oxidative coupling reaction on phenolic compounds and toluene compounds. According to the method, the iron (III) complex is used as the catalyst for the first time, and oxidative coupling of the phenolic compound and the toluene compound is realized. The method is the first oxidative coupling reaction of phenolic compounds and benzyl C(sp3)-H bonds, and a new method is provided for synthesizing aryl benzyl ether compounds. Compared with an existing synthesis method, the method provided by the invention avoids using toxic and polluting halogenated hydrocarbon and strong base, has better atom economy, and conforms to the development concept of green synthetic chemistry.

Towards ortho-selective electrophilic substitution/addition to phenolates in anhydrous solvents

Alkyl-substituted Li-phenolates with BnBr in water solution lead to a mixture of o- and p-Bn-substituted phenols together with a substantial amount of phenol Bn ether. In CPME, and especially in toluene with 1–2 equivalents of ether or alcohol additives, ortho-selective alkylation is achieved. In the case of o,o,p-tri- and o,o-di-substituted phenols dearomatization occurs affording o-Bn-substituted alkyl cyclohexadienones with yields up to 92% with an o/p ratio up to 90/1.

Transition-Metal-Free and Base-Promoted Carbon-Heteroatom Bond Formation via C-N Cleavage of Benzyl Ammonium Salts

A facile and general method for constructing carbon-heteroatom (C-P, C-O, C-S, and C-N) bonds via C-N cleavage of benzyl ammonium salts under transition-metal-free conditions was reported. The combination of t-BuOK and 18-crown-6 enabled a wide range of substituted benzyl ammonium salts to couple readily with different kinds of heteroatom nucleophiles, i.e. hydrogen phosphoryl compounds, alcohols, thiols, and amines. Good functional group tolerance was demonstrated. The scale-up reaction and one-pot synthesis were also successfully performed.

Jet Colliding and Mixing Efficiency

Two experimental methods, the Nile Red dye extraction and the Williamson ether synthesis in biphasic conditions, were used to characterize the mixing performance of a new cheap impinging jet colliding mixer from Gjosa and to compare it to other commercial

Metal-Free C-O Bond Functionalization: Catalytic Intramolecular and Intermolecular Benzylation of Arenes

A catalytic, metal-free intramolecular rearrangement of benzyl phenyl ethers using nitrosonium salt as a catalyst is described. The optimized reaction conditions enabled a catalytic and metal-free Friedel-Crafts alkylation reaction with benzylic alcohols, producing water as the stoichiometric byproduct. A comprehensive scope (>50 examples) for both approaches and application in drug synthesis were demonstrated. Mechanistic studies suggest a Lewis acid-based mechanism for the metal-free Friedel-Crafts reaction.

Exploring the Reactivity of α-Lithiated Aryl Benzyl Ethers: Inhibition of the [1,2]-Wittig Rearrangement and the Mechanistic Proposal Revisited

By carefully controlling the reaction temperature, treatment of aryl benzyl ethers with tBuLi selectively leads to α-lithiation, generating stable organolithiums that can be directly trapped with a variety of selected electrophiles, before they can undergo the expected [1,2]-Wittig rearrangement. This rearrangement has been deeply studied, both experimentally and computationally, with aryl α-lithiated benzyl ethers bearing different substituents at the aryl ring. The obtained results support the competence of a concerted anionic intramolecular addition/elimination sequence and a radical dissociation/recombination sequence for explaining the tendency of migration for aryl groups. The more favored rearrangements are found for substrates with electron-poor aryl groups that favor the anionic pathway.

Silica-Supported Oligomeric Benzyl Phosphate (Si-OBP) and Triazole Phosphate (Si-OTP) Alkylating Reagents

The syntheses of silica-supported oligomeric benzyl phosphates (Si-OBPn) and triazole phosphates (Si-OTPn) using ring-opening metathesis polymerization (ROMP) for use as efficient alkylating reagents is reported. Ease of synthesis and grafting onto the surface of norbornenyl-tagged (Nb-tagged) silica particles has been demonstrated for benzyl phosphate and triazole phosphate monomers. It is shown that these silica polymer hybrid reagents, Si-OBPn and Si-OTPn, can be used to carry out alkylation reactions with an array of different nucleophiles to afford the corresponding benzylated and (triazolyl)methylated products in good yield and high purity.

Choline chloride based deep eutectic solvent as an efficient solvent for the benzylation of phenols

Deep eutectic solvents (such as the combination of urea and choline chloride) are found to be promising solvent and phase-transfer-media for benzylation of phenol. These methods avoided the complexity of multiple alkylations giving selectively O-alkylated aromatic products. Good to excellent yields of the corresponding benzyl phenyl ether were obtained. The non-toxic, biodegradable, inexpensive, and recyclable nature of DES make this protocol green and cost-effective.

Tetrabutyl ammonium bromide-mediated benzylation of phenols in water under mild condition

Benzylation of phenol was successfully achieved in water under room temperature mediated by tetrabutylammonium bromide (TBAB) for only 2 h affording the corresponding benzyl phenyl ether with good to excellent yields. This protocol is very efficient, simple, avoiding catalysts, easy to work-up after reaction, and especially 'green'.