98-17-9Relevant academic research and scientific papers
A mild and practical method for deprotection of aryl methyl/benzyl/allyl ethers with HPPh2andtBuOK
Pan, Wenjing,Li, Chenchen,Zhu, Haoyin,Li, Fangfang,Li, Tao,Zhao, Wanxiang
, p. 7633 - 7640 (2021/09/22)
A general method for the demethylation, debenzylation, and deallylation of aryl ethers using HPPh2andtBuOK is reported. The reaction features mild and metal-free reaction conditions, broad substrate scope, good functional group compatibility, and high chemical selectivity towards aryl ethers over aliphatic structures. Notably, this approach is competent to selectively deprotect the allyl or benzyl group, making it a general and practical method in organic synthesis.
Synthetic method of m-trifluoromethylphenol
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Paragraph 0022; 0026-0029; 0032-0034; 0037-0041, (2021/11/03)
The invention belongs to the field of organic synthesis, and particularly relates to a synthetic method of m-trifluoromethylphenol. The method comprises the following steps: (1) in a solvent, carrying out Williamson reaction on m-chlorobenzotrifluoride and tert-butyl alcohol under the catalysis of sodium hydride and metal acetate to prepare an intermediate m-trifluoromethylbenzene tert-butyl ether; (2) in a solvent, carrying out tertiary butyl removal on the m-trifluoromethyl benzene tert-butyl ether prepared in the step (1) under the action of a ZSM-5 molecular sieve to prepare the trifluoromethylphenol. The synthesis steps are simple, the cost is low, and the process is more environment-friendly.
Method for hydrolyzing diarylether compound to generate aryl phenol compound
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Paragraph 0082-0085, (2021/09/29)
The invention discloses a method for hydrolyzing a diarylether compound to generate an arylphenol compound. According to the method, visible light is utilized to excite a photosensitizer for catalysis. In a reaction solvent, the raw material in the formula (1) breaks a C (sp2)-O bond under the auxiliary action of acid, and hydrolysis is performed to obtain the bimolecular aryl phenol compounds in the formula (3) and the formula (4). The method can catalyze the reaction at room temperature, is green and environment-friendly, and is easy to operate; the universality is wide, the reaction yield is relatively high, and the tolerance of functional groups is strong; the synthesis method not only can realize small-scale hydrolysis conversion of various diarylether compounds, but also can realize hydrolysis of herbicidal ether, triclosan and a lignin template substrate, and even can realize large-scale hydrolysis of triclosan and the lignin template substrate to realize gram-level degradation. A new strategy is provided for recovering phenol derivatives through lignin hydrolysis, degrading pesticides and purifying wastewater containing a degerming agent or herbicide. The method has wide application prospect and use value.
Highly efficient heterogeneous V2O5@TiO2 catalyzed the rapid transformation of boronic acids to phenols
Upadhyay, Rahul,Singh, Deepak,Maurya, Sushil K.
supporting information, p. 3925 - 3931 (2021/08/24)
A V2O5@TiO2 catalyzed green and efficient protocol for the hydroxylation of boronic acid into phenol has been developed utilizing environmentally benign oxidant hydrogen peroxide. A wide range of electron-donating and the electron-withdrawing group-containing (hetero)aryl boronic acids were transformed into their corresponding phenol. The methodology was also applied successfully to transform various natural and bioactive molecules like tocopherol, amino acids, cinchonidine, vasicinone, menthol, and pharmaceuticals such as ciprofloxacin, ibuprofen, and paracetamol. The other feature of the methodology includes gram-scale synthetic applicability, recyclability, and short reaction time.
Aryl phenol compound as well as synthesis method and application thereof
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Paragraph 0096-0099, (2021/05/12)
The invention discloses a synthesis method of an aryl phenol compound shown as a formula (3). All systems are carried out in an air or nitrogen atmosphere, and visible light is utilized to excite a photosensitizer for catalyzation. In a reaction solvent, ArNR1R2 as shown in a formula (1) and water as shown in a formula (2) are used as reaction raw materials and react under the auxiliary action of acid to obtain the aryl phenol compound as shown in a formula (3). The ArNR1R2 in the formula (1) can be primary amine and tertiary amine, can also be steroid and amino acid derivatives, and can also be drugs or derivatives of propofol, paracetamol, ibuprofen, oxaprozin, indomethacin and the like. The synthesis method has the advantages of cheap and easily available raw materials, simple reaction operation, mild reaction conditions, high reaction yield and good compatibility of substrate functional groups. The fluid reaction not only can realize amplification of basic chemicals, but also can realize amplification of fine chemicals, such as synthesis of drugs propofol and paracetamol. The invention has wide application prospect and use value.
Method for preparing alcohol and phenol through aerobic hydroxylation reaction of boric acid derivative in absence of photocatalyst
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Paragraph 0025-0028; 0030-0032, (2020/01/25)
The invention discloses a method for preparing alcohol and phenol through aerobic hydroxylation reaction of a boric acid derivative in the absence of a photocatalyst, wherein the boric acid derivativeis aryl boronic acid or alkyl boronic acid, and the corresponding target compounds are respectively a phenol-based compound and an alcohol-based compound. According to the method, by using a boric acid derivative as a reaction substrate, an additive is added under a solvent condition, and a hydroxylation reaction is performed under aerobic and illumination conditions to obtain a corresponding target compound. According to the invention, the new strategy is provided for the synthesis of phenols through aerobic hydroxylation of aryl boronic acid without a photocatalyst; the catalyst-free aerobic hydroxylation method for photocatalysis of aryl boronic acid or alkyl boronic acid by using triethylamine as an additive is firstly disclosed; and the new method has advantages of photocatalyst-freecondition, wide substrate range and good functional group compatibility.
Nickel-catalyzed removal of alkene protecting group of phenols, alcohols via chain walking process
Meng, Chenkai,Niu, Haolin,Ning, Juehan,Wu, Wengang,Yi, Jun
, (2020/02/04)
An efficient nickel-catalyzed removal of alkene protection group under mild condition with high functional group tolerance through chain walking process has been established. Not only phenolic ethers, but also alcoholic ethers can be tolerated with the retention of stereocenter adjacent to hydroxyl group. The new reaction brings the homoallyl group into a start of new type of protecting group.
Aerobic photooxidative hydroxylation of boronic acids catalyzed by anthraquinone-containing polymeric photosensitizer
Chen, Yang,Ding, Aishun,Hu, Jianhua
, p. 7927 - 7932 (2020/03/11)
We report herein the synthesis of a polymeric photosensitizer and its application in aerobic photooxidative hydroxylation of boronic acids. The polymeric photosensitizer was synthesized by the condensation of anthraquinone-2-carbonyl chloride (AQ-2-COCl) with poly (2-hydroxyethyl methacrylate) (PHEMA). The photo-oxidative hydroxylation of boronic acids using anthraquinone-containing-poly (2-hydroxyethyl methacrylate) (AQ-PHEMA) was then explored and shown to exhibit high efficiency and broad scope. Moreover, AQ-PHEMA could be easily recovered and reused for more than 20 times without significant loss of the catalytic activity.
Preparation method of m-trifluoromethylphenol
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Paragraph 0051-0055, (2020/03/02)
The invention discloses a preparation method of m-trifluoromethylphenol. The preparation method of the m-trifluoromethylphenol comprises the steps that (1) in a continuous flow reactor, a sulfate aqueous solution and an aqueous solution of sodium nitrite are subjected to a diazotization reaction to obtain a diazonium salt solution, wherein the sulfate aqueous solution is a mixture of an aqueous solution of sulfuric acid and m-trifluoromethyl aniline; and (2) in the continuous flow reactor, under the existence of an aromatic solvent, the diazonium salt solution obtained in the step (1) is subjected to a hydrolysis reaction to obtain the m-trifluoromethylphenol, wherein the temperature of the hydrolysis reaction is 101-200 DEG C. Through the continuous preparation method, the reaction concentration can be increased, the reaction time can be greatly shortened, production efficiency is improved, the safety risk is lowered, the yield can reach 95% or above, the purity can reach 99.5% or above, and the method has the advantages of being easy and convenient to operate, safer, more environmentally friendly, lower in cost and the like.
Method of removing protective groups of olefins under catalytic action of nickel
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Paragraph 0227-0230, (2019/10/04)
The invention relates to a method of removing protective groups of olefins under the catalytic action of nickel. The method comprises following steps: dissolving olefin containing compounds into an organic solvent, carrying out reactions in the presence of a catalyst, organic ligands, bis(pinacolato)diboron, alkalis, alcohols, and water, wherein the catalyst contains nickel; after reactions, adding excess hydrochloric acid solution (1M) to adjust the pH to the acidic region, stirring the solution until the solution becomes clear; adding water and ethyl acetate to carry out extraction; washing the organic phase by saturated brine, drying the organic phase by anhydrous sodium sulfate, carrying out condensation, and adopting a 200-300 mesh silica gel column to carry out chromatographic separation to obtain compounds that contains alcohols or phenol. The provide method has the advantages that the adopted chemical reagents are common, the primary alkyl halide protective groups of olefins can be removed efficiently, and the method has a good application prospect in the field of organic synthesis and good industrial potential.
