118-55-8Relevant articles and documents
Copper-Catalyzed Selective Diphenylation of Carboxylic Acids with Cyclic Diaryliodonium Salts
Xie, Hao,Yang, Shuai,Zhang, Chunxia,Ding, Mingruo,Liu, Min,Guo, Jie,Zhang, Fengzhi
, p. 5250 - 5262 (2017)
Herein, we describe a novel one-step copper-catalyzed diphenylation of readily available aliphatic or (hetero)aromatic carboxylic acids with cyclic hypervalent diaryliodonium reagents. The selective diphenylation of benzoic acids with high atom economy can be achieved without observation of the arylation at the phenyl hydroxyl/thio/amino position. The valuable biphenyl esters with an additional iodo-substituent were obtained in good to excellent yields, which can be further transformed to diversified building blocks for the synthesis of bioactive natural products, pharmaceuticals, and functional materials. A wide range of different functional groups are compatible under the optimized reaction conditions.
Cu(OTf)2-mediated Chan-Lam reaction of carboxylic acids to access phenolic esters
Zhang, Lingli,Zhang, Guoying,Zhang, Manli,Cheng, Jiang
, p. 7472 - 7474 (2010)
A Cu(OTf)2-mediated Chan-Lam reaction of carboxylic acids with arylboronic acids is described. It represents a facile and practical methodology to access phenolic esters in moderate to good yields. The procedure tolerates a series of functional groups, such as methoxycarbonyl, acetoxy, free phenolic hydroxyl, vinyl, nitro, trifluoromethyl, methoxyl, bromo, chloro, iodo, and acetyl groups.
Synthesis, characterization and catalytic activity studies on cordierite honeycomb coated with ZrO2 based solid super acids
Mohamed Shamshuddin,Shyam Sundar,Thimmaraju,Venkatesh,Vatsalya,Senthilkumar
, p. 799 - 807 (2012)
Cordierite honeycomb coated with solid acids such as ZrO2, Mo/ZrO2 and W/ZrO2 were synthesized. These solid acid catalysts were also synthesized in their powder forms. The catalytic materials were characterized for their physicochemical properties such as surface area, surface acidity, crystallinity and morphology by using techniques such as BET, NH3-TPD/n-butylamine back titration, powder XRD and SEM respectively. The catalytic activity of these catalytic materials was determined in an acid catalyzed transesterification reaction of methyl salicylate with phenol to synthesize phenyl salicylate (salol). The effect of concentration of Mo or W ions on ZrO2, nature of the catalyst (whether honeycomb coated or powder form), reaction temperature, reaction time and reusability of the catalytic material in transesterification was studied. Formation of diphenyl ether as a by-product was observed on increasing the concentration of Mo or W ions on ZrO2 and also at higher reaction temperature. The catalytic activity of catalytic materials was correlated with surface acidity and the crystalline phases of catalytic material. Transesterification reactions were also carried out with methyl salicylate and benzyl alcohol or cyclohexanol to synthesize their respective salicylate esters. A probable mechanism of transesterification of methyl salicylate with an alcohol is also proposed. The honeycomb catalysts were found to be efficient, ecofriendly, economical and reusable catalysts compared to their powder forms.
Synthesis of phenyl esters using SiO2-SO3H catalyst in conventional heating and microwave-irradiated esterification processes
Barbosa, Sandro L.,Ottone, Myrlene,De Freitas, Milton,Lima, Camila D.,Nelson, David L.,Clososki, Giuliano C.,Caires, Franco J.,Klein, Stanlei I.,Hurtado, Gabriela R.
, p. 3663 - 3668 (2019)
A SiO2-SO3H amorphous catalyst containing a small surface area of 115.0 m2g-1 and 1.32 mmol H+/g was prepared from fine construction sand and sodium carbonate and sulfonated with H2SO4. In a 10% (w/w) basis, it is very efficient for catalyzing the esterification of carboxylic acids with phenol. The reaction processes were performed using conventional heating and under microwave irradiation. The yields were higher in the microwave-irradiated esterification. The catalyst could be used for three esterification sequences in both processes.
Synthesis of salicylates from anionically activated aromatic trifluoromethyl group
Lin, Chuankai,Liu, Jin-Biao,Wang, Ruixiang,Xie, Huilin
supporting information, (2021/12/22)
An efficient approach to salicylates via a novel transformation of anionically activated aromatic trifluoromethyl group is described. Anionically activated trifluoromethyl group can react with phenols/alcohols under alkaline conditions to afford aryl/alkyl salicylates in high yields. Mechanism studies indicate that the carbonyl oxygen atom of ester is from the H2O in the solvent.
Cerium photocatalyzed radical smiles rearrangement of 2-aryloxybenzoic acids
Tripathy, Alisha Rani,Yatham, Veera Reddy,Yedase, Girish Suresh
, p. 25207 - 25210 (2021/08/05)
We report herein a cerium photocatalyzed aryl migration from an aryl ether to a carboxylic acid group through radical-Smiles rearrangement. This operationally simple protocol utilizes inexpensive CeCl3as a photocatalyst and converted a variety of 2-aryloxybenzoic acids into aryl-2-hydroxybenzoates in good yields.
Production process of phenyl salicylate
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Paragraph 0023-0038, (2020/09/23)
The invention discloses a production process of phenyl salicylate, and relates to the field of production of phenyl salicylate. The production process mainly comprises the following steps: mixing diphenyl carbonate and a catalyst, heating to 180-260 DEG C, and reacting for 2-14 h to obtain phenyl salicylate. By adopting the technical scheme, diphenyl carbonate can be converted into phenyl salicylate through a one-step reaction, so that the subsequent application of diphenyl carbonate is broadened, and the production efficiency of phenyl salicylate is improved.
Rhodium-Catalyzed Carbonylative Synthesis of Aryl Salicylates from Unactivated Phenols
Ai, Han-Jun,Zhang, Youcan,Zhao, Fengqian,Wu, Xiao-Feng
supporting information, p. 6050 - 6054 (2020/10/02)
A rhodium-catalyzed carbonylative transformation of unactivated phenols to aryl salicylates is described. This protocol is characterized by utilizing 1,3-rhodium migration as the key step to provide direct access to synthesize ohydroxyaryl esters. Various desired aryl o-hydroxybenzoates were produced in moderate to excellent yields with bis(dicyclohexylphosphino)ethane (DCPE) as the ligand. Interestingly, diphenyl carbonate was formed as the main product when 1,3-bis(diphenylphosphino)propane (DPPP) was used as the ligand. A plausible reaction mechanism is proposed.
Influence of coordinating groups of organotin compounds on the Fries rearrangement of diphenyl carbonate
Liu, Tao,Yuan, Xiaoxue,Zhang, Gang,Zeng, Yi,Chen, Tong,Wang, Gongying
, p. 28112 - 28118 (2019/09/30)
In this paper, the Fries rearrangement of diphenyl carbonate (DPC) catalyzed by organotin compounds with different coordination groups was studied for the first time. The electronic effect and steric hindrance of the coordinating groups were discussed with respect to the reactivity of DPC rearrangement. The results showed that both the electronic effect and steric hindrance of the coordinating groups influenced the acidity of the active tin centers and then affected the catalytic performance of organotin as a Lewis acid for the rearrangement of DPC, and the influence of the electronic effect is greater than that of steric hindrance. The catalytic activity is in the order of BuSnO(OH) > Bu2SnO > Bu2Sn(OCOC11H23)2 > BuSnCl3 > Bu3SnOSnBu3 > Bu3SnCl, and Bu2SnO showed the best catalytic activity due to its strong electron absorption effect, small steric hindrance, and good stability. Under the optimum reaction conditions, the conversion of DPC was up to 93%, and the yields of phenyl salicylate (PS) and xanthone (XA) were 62% and 28%, respectively. In addition, a reaction mechanism of DPC rearrangement catalyzed by the organotin compounds was speculated. This research can provide vigorous theoretical data support to control the byproducts produced by DPC rearrangement in the process of DPC synthesis. It also provides a new route for the preparation of PS and XA.
Efficient Aryl Migration from an Aryl Ether to a Carboxylic Acid Group To Form an Ester by Visible-Light Photoredox Catalysis
Wang, Shao-Feng,Cao, Xiao-Ping,Li, Yang
supporting information, p. 13809 - 13813 (2017/10/24)
We have developed a highly efficient aryl migration from an aryl ether to a carboxylic acid group through retro-Smiles rearrangement by visible-light photoredox catalysis at ambient temperature. Transition metals and a stoichiometric oxidant and base are avoided in the transformation. Inspired by the high efficiency of this transformation and the fundamental importance of C?O bond cleavage, we developed a novel approach to the C?O cleavage of a biaryl ether to form two phenolic compounds, as demonstrated by a one-pot, two-step gram-scale reaction under mild conditions. The aryl migration exhibits broad scope and can be applied to the synthesis of pharmaceutical compounds, such as guacetisal. Primary mechanistic studies indicate that the catalytic cycle occurs by a reductive quenching pathway.
