14210-97-0Relevant academic research and scientific papers
Synthesis, crystal structures and DFT calculations of two new phenol-based ester derivatives
Ganaie, Javeed A.,Kumar, Jubin,Butcher, Ray J.,Jasinski, Jerry P.,Gupta, Sushil K.
, p. 93 - 104 (2016)
Two new phenol-based ester derivatives, namely C13H9ClO2 (I) and C20H14O4 (II) have been synthesized and characterized by NMR spectroscopy, single crystal X-ray diffraction and density functional theory (DFT) geometry optimization and molecular orbital calculations. Compound I crystallizes in the orthorhombic space group Pca2(1),with a = 7.6297 (5) ?, b = 5.5875 (3) ?, c = 26.1624 (12) ?, α = β = γ = 90°, V = 1115.33(11) ?3 and Z = 4. Compound II crystallizes in the triclinic space group P $βar 1$$ 1 ˉ, with a = 5.7970 (4) ?, b = 8.1366 (8) ?, c = 8.8057 (9) ?, α = 83.246 (8)°, β = 72.138 (8)°, γ = 76.696 (8)°, V = 384.22 (6) ?3 and Z = 1. Geometry optimization calculations for each compound is consistent with these observations. A comparison of the dihedral angles between mean planes of the benzene rings in the crystal with the DFT theoretical calculations and weak intermolecular hydrogen bond interactions has been included for each molecule. Electronic transitions have been predicted by DFT Molecular Orbital calculations and compared with experimental absorption spectra.
Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters
Huang, Changyu,Li, Jinpeng,Wang, Jiaquan,Zheng, Qingshu,Li, Zhenhua,Tu, Tao
, p. 66 - 71 (2020/11/18)
The amide C-N cleavage has drawn a broad interest in synthetic chemistry, biological process and pharmaceutical industry. Transition-metal, luxury ligand or excess base were always vital to the transformation. Here, we developed a transition-metal-free hydrogen-bond-assisted esterification of amides with only catalytic amount of base. The proposed crucial role of hydrogen bonding for assisting esterification was supported by control experiments, density functional theory (DFT) calculations and kinetic studies. Besides broad substrate scopes and excellent functional groups tolerance, this base-catalyzed protocol complements the conventional transition-metal-catalyzed esterification of amides and provides a new pathway to catalytic cleavage of amide C-N bonds for organic synthesis and pharmaceutical industry. [Figure not available: see fulltext.]
Solid-Phase Benzoylation of Phenols and Alcohols in Microwave Reactor: An Ecofriendly Protocol
Chakraborty, Suchandra,Saha, Ahana,Basu, Kaushik,Saha, Chandan
supporting information, p. 2331 - 2343 (2015/10/12)
An efficient solid-phase benzoylation of phenols and alcohols was developed under microwave irradiation. A stoichiometric amount of benzoyl chloride was sufficient to carry out the reaction. This benzoylation features short reaction time, good yields, and easy workup procedures. Furthermore, the scope of the reaction was extended to prepare 3,5-dinitrobenzoyl derivatives of alcohols.
The first vinyl acetate mediated organocatalytic transesterification of phenols: A step towards sustainability
Kumar, Manoj,Bagchi, Sourav,Sharma, Anuj
, p. 8329 - 8336 (2015/11/10)
The present report outlines our efforts toward a simple yet elegant protocol for O-acylation of a wide variety of phenols. This highly enabling and solventless method relies on vinyl acetate as an innocuous acyl donor and DABCO as an organocatalyst. Operational simplicity, excellent yields, higher and faster conversion rates without excess reagents, a simple workup and essentially no need of columns are some of the salient features of the reported protocol.
Synthesis of industrially important aromatic and heterocyclic ketones using hierarchical ZSM-5 and Beta zeolites
Kore, Rajkumar,Srivastava, Rajendra,Satpati, Biswarup
, p. 129 - 141 (2015/09/28)
Hierarchical ZSM-5 and Beta zeolites were investigated in the synthesis of wide range of industrially important aromatic/heterocyclic ketones by Friedel-Crafts acylation and benzoylation reactions. For comparative study, conventional ZSM-5 and Beta, and amorphous mesoporous Al-MCM-41 were investigated. Hierarchical zeolites were prepared by multi-ammonium structure directing agents whereas conventional zeolites were prepared by mono-ammonium structure directing agents. Among the catalysts investigated in this study, hierarchical Beta exhibited the highest reactant conversion in the acylation and benzoylation reactions. In this study, the systematic assessment of the catalytic activity of acid catalysts for wide range of aromatic and heterocyclic compounds is shown under one umbrella. To the best of our knowledge, these reactions over hierarchical zeolites (ZSM-5 and Beta) are reported here for the first time. Structure activity relationship is explained based on the physico-chemical properties, molecular size, reactivity of reactants, and reaction mechanism. Catalysts can be easily recovered and reused with negligible loss in the catalytic activity.
HF-Pyridine: A versatile promoter for monoacylation/sulfonylation of phenolic diols and for direct conversion of t-butyldimethylsilyl ethers to the corresponding acetates
Michigami, Kyosuke,Yoshimoto, Kazuya,Hayashi, Masahiko
scheme or table, p. 138 - 139 (2012/03/09)
Monoacylation and trifluoromethanesulfonylation of phenolic diols were achieved by the aid of HF-pyridine, whereas diacylation occurred with pyridine alone. Furthermore, HF-pyridine was found to promote the direct conversion of t-butyldimethylsilyl ethers to the corresponding acetates.
Molybdenum hexacarbonyl mediated alkoxycarbonylation of aryl halides
Ren, Wei,Emi,Yamane, Motoki
experimental part, p. 2303 - 2309 (2011/09/19)
Mo(CO)mediates the alkoxycarbonylation of aryl halides in their reaction with alcohols to afford arenecarboxylic acid esters. The molybdenum carbonyl complexes act as the catalyst and the source with carbon monoxide. The alkoxycarbonylation proceeds with a small excess of carbon monoxide in the form of Mo(CO)and the procedure is simple compared to the conventional method, which uses palladium catalyst under gaseous carbon monoxide. Using this procedure, a variety of carboxylic acid esters were prepared. Georg Thieme Verlag Stuttgart ? New York.
A simple and efficient transprotection of aryl methyl ether to aryl benzoate under microwave activation
Marette, Caroline,Larrouquet, Camille,Tisnès, Pierre,Deloye, Jean-Bernard,Gras, Emmanuel
, p. 6947 - 6950 (2007/10/03)
A simple and efficient method for the transprotection of aryl methyl ether to easily cleavable arylbenzoate mediated by microwave activation has been developed. One important feature of this method is its high tolerance towards sensitive functionalities and to some extent to bulky environment.
Magnesium bistrifluoromethanesulfonimide as a new and efficient acylation catalyst
Chakraborti, Asit K.,Shivani
, p. 5785 - 5788 (2007/10/03)
Magnesium bistrifluoromethanesulfonimide catalyzed the acetylation of phenols, alcohols, and thiols under solvent-free conditions at room temperature and in short times. Electron-deficient and sterically hindered phenols provided excellent yields. The catalyst was found to be general for acylation with other anhydrides, such as propionic, isobutyric, pivalic, chloroacetic, and benzoic anhydrides. The rate of acylation was influenced by the electronic and steric factors associated with the anhydride. The reaction with less electrophilic anhydrides (e.g., chloroacetic and benzoic anhydrides) required higher temperature (～80 °C). Chemoselective acetylation, pivalation, and benzoylation took place with acid-sensitive alcohols without any competitive dehydration/rearrangement.
3,6-Dibenzoxyl-1,2-pyridazine: A new versatile benzoyl transferring agent for NH2, -OH and -SH benzoylations
Mashraqui, Sabir Hussain,Shivaji, Jadhav Latika
, p. 927 - 935 (2007/10/03)
A newly synthesized 3,6-dibenzoxyl-1,2-pyridazine 3 has been investigated for its potential to transfer the benzoyl group to various organic substrates carrying -NH2, -OH and -SH groups. The benzoyl transfer is fairly general in scope, occurs under convenient conditions and provides good to excellent yields of benzoylated products. Moreover, by choosing proper conditions, it is possible to achieve chemoselective benzoylation in bi-functional molecules. For instance, N-benzoylation of aromatic amines can be selectively accomplished over that of aliphatic amines and vice versa by manipulating reaction conditions. Selective N- or O-benzoylation in aminophenols is also possible. Although, not studied in detail, we final that dibenzoate 3 can also be used to effect C-benzoylation of reactive phenols and ketones, as exemplified by the C-benzoylation of resorcinol and acetophenone, respectively. Dibenzoate 3, besides being a crystalline, easy to handle, solid possesses twice the potential as an acyl carrier compared to the other known acyl carriers. These features make 3 as an attractive choice for many applications pertaining to benzoyl transfer reactions.
