93-18-5Relevant academic research and scientific papers
Cross-Coupling Reactions of Aryl Halides with Primary and Secondary Aliphatic Alcohols Catalyzed by an O,N,N-Coordinated Nickel Complex
Hashimoto, Toru,Shiota, Keisuke,Funatsu, Kei,Yamaguchi, Yoshitaka
supporting information, p. 1625 - 1630 (2021/01/26)
A synthesis of alkyl aryl ethers was achieved via the cross-coupling of aryl halides with primary and secondary aliphatic alcohols catalyzed by a bench-stable nickel complex supported by a monoanionic O,N,N-tridentate ligand. This nickel-catalyzed reaction proceeds smoothly in the absence of a phosphine ligand, affording alkyl aryl ethers in moderate to good yields. (Figure presented.).
Mustard Carbonate Analogues as Sustainable Reagents for the Aminoalkylation of Phenols
Annatelli, Mattia,Trapasso, Giacomo,Salaris, Claudio,Salata, Cristiano,Castellano, Sabrina,Aricò, Fabio
supporting information, p. 3459 - 3464 (2021/05/24)
N,N-dialkyl ethylamine moiety can be found in numerous scaffolds of macromolecules, catalysts, and especially pharmaceuticals. Common synthetic procedures for its incorporation in a substrate relies on the use of a nitrogen mustard gas or on multistep syntheses featuring chlorine hazardous/toxic chemistry. Reported herein is a one-pot synthetic approach for the easy introduction of aminoalkyl chain into different phenolic substrates through dialkyl carbonate (β-aminocarbonate) chemistry. This new direct alcohol substitution avoids the use of chlorine chemistry, and it is efficient on numerous pharmacophore scaffolds with good to quantitative yield. The cytotoxicity via MTT of the β-aminocarbonate, key intermediate of this synthetic approach, was also evaluated and compared with its alcohol precursor.
Light assisted O-alkylation of phenols to ethers using layered double oxides catalyst under green and mild conditions
Wang, Ruiyi,Wang, Xiaoyu,Zheng, Zhanfeng
, (2020/07/03)
O-alkylation of phenols with dialkyl carbonates to ethers over layered double oxides (LDOs) catalyst under light irradiation is described. A base additive is not required when using the longer-chain diethyl carbonate as an alkylating agent owing to the sufficient basicity provided by LDOs. The synergism of substrate phenols molecules absorbing light to reach the first excited states with acid–base pairs of catalyst enhanced the interaction of reactant molecules with the surface of LDOs, simultaneously accelerating the cleavage of phenolic hydroxyl groups. A variety of phenols are tolerated in this system. This work reports a simple and environmentally benign catalytic process for the dehydrogenation of phenolic hydroxyl groups.
A new alkylation of aryl alcohols by boron trifluoride etherate
Jumbam, Ndze Denis,Maganga, Yamkela,Masamba, Wayiza,Mbunye, Nomthandazo I.,Mgoqi, Esethu,Mtwa, Sphumusa
, (2019/10/28)
The ethylation of aryl alcohols by an ethyl moiety of boron trifluoride etherate is described. The reaction proceeded cleanly and afforded good yields of the corresponding aryl ethyl ethers. It tolerated the presence of functional groups such as aryl, alkyl, halogens, nitro, nitrile, and amino. However, the presence of amino or nitro groups ortho to a hydroxyl group of an aryl compound drastically reduced the yields of the anticipated products due to the chelation of the aforementioned functional groups with boron trifluoride etherate. A nitrogen atom in the aromatic ring system, as exemplified by hydroxypyridine and 8-hydroxyquinoline, completely inhibited the reaction. Resorcinol, hydroquinone, and aryl alcohols with aldehyde functions decomposed under the reaction conditions.
Method for synthesizing alkyl-2-naphthyl ether
-
Paragraph 0016; 0017, (2019/01/14)
The invention discloses a method for synthesizing alkyl-2-naphthyl ether. 2-naphthol, a catalyst and dialkyl carbonate are heated to 110-120 DEG C, dialkyl carbonate is added dropwise, a mixed solution of dialkyl carbonate and corresponding alcohol is fractionated out during dropwise addition, the temperature is controlled not to exceed 200 DEG C, reaction is stopped when conversion of 2-naphtholreaches 95% or higher, inorganic boric acid and a dehydration solvent are added, unreacted 2-naphthol is removed, and rectification or recrystallization is performed, and a pure product is obtained. The process route has little corrosion to equipment, few 'three wastes' emissions and low environmental pollution.
Nickel-Catalyzed Deamidative Step-Down Reduction of Amides to Aromatic Hydrocarbons
Dey, Aniruddha,Sasmal, Sheuli,Seth, Kapileswar,Lahiri, Goutam Kumar,Maiti, Debabrata
, p. 433 - 437 (2017/06/05)
To date, cleavage of the C-N bond in aromatic amides has been achieved in molecules with a distorted constitutional framework around the nitrogen atom. In this report, a nickel-catalyzed reduction of planar amides to the corresponding lower hydrocarbon homologue has been reported. This involves a one-pot reductive cleavage of the C-N bond followed by a tandem C-CO bond break in the presence of a hydride source. Substrate scope circumscribes deamidation examples which proceed via oxidative addition of nickel in the amide bonds of nontwisted amides. Mechanistic studies involving isolation and characterization of involved intermediates via different spectroscopic techniques reveal a deeper introspection into the plausible catalytic cycle for the methodology.
Method for compounding drug intermediate 2-ethoxy naphthalene of sodium nafcillin
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Paragraph 0015; 0016, (2016/11/17)
The invention discloses a method for compounding drug intermediate 2-ethoxy naphthalene of sodium nafcillin. The method comprises the following steps: adding 1.2 mol of beta-naphthol and 230 to 260 ml of ethylamine in a reaction vessel which is provided with a stirrer and a reflux condenser, controlling the stirring speed to be 130 to 170 rpm, slowly adding 110 ml of phosphoric acid solution, rising the solution temperature to be 80 to 86 DEG C, carrying out reflux for 15 to 17 hours, pouring the solution into a 1.5-L sodium sulfite solution after cooling, stirring for 90 to 120 minutes, separating crystals out, filtering, washing by a saline solution, washing by acetamide, recrystallizing in ethyl acetate, dissolving the crystals in chlorobenzene, carrying out decompression distillation, collecting a distillate at 120 to 129 DEG C, and obtaining 2-ethoxy naphthalene, wherein the mass percentage of ethylamine in the steps is 90 to 95 percent, the mass percentage of the phosphoric acid solution in the steps is 45 to 50 percent, and the saline solution in the steps is any one of potassium bromide and sodium sulfate.
Microwave-Assisted solid-liquid phase alkylation of naphthols
Balint, Erika,Kovacs, Orsolya,Drahos, Laszlo,Keglevich, Gyoergy
, p. 330 - 336 (2013/07/26)
The microwave promoted alkylation of 1- and 2-naphthols with benzyl, butyl, ethyl and isopropyl halides in the presence of an alkali carbonate may result in O- and C-Alkylated products. The alkylations were O-selective in the presence of K2CO3 in acetonitrile as the solvent and in the absence of phase transfer catalyst. The alkylations utilizing butyl and ethyl halides were also O-selective in solventless accomplishment and in the presence of triethylbenzylammonium chloride.
Iridium-catalyzed, intermolecular hydroetherification of unactivated aliphatic alkenes with phenols
Sevov, Christo S.,Hartwig, John F.
supporting information, p. 9303 - 9306 (2013/07/26)
Metal-catalyzed addition of an O-H bond to an alkene is a desirable process because it allows for rapid access to ethers from abundant starting materials without the formation of waste, without rearrangements, and with the possibility to control the stereoselectivity. We report the intermolecular, metal-catalyzed addition of phenols to unactivated α-olefins. Mechanistic studies of this rare catalytic reaction revealed a dynamic mixture of resting states that undergo O-H bond oxidative addition and subsequent olefin insertion to form ether products.
An efficient copper-catalyzed etherification of aryl halides
Huang, Jinkun,Chen, Ying,Chan, Johann,Ronk, Mike L.,Larsen, Robert D.,Faul, Margaret M.
experimental part, p. 1419 - 1422 (2011/07/30)
An efficient and mild copper-catalyzed ether formation from aryl halides and aliphatic alcohols has been developed. The key to the successful coupling is the use of lithium alkoxide, directly or in situ generated by lithium tert-butoxide, and the corresponding alcohol as solvent. Georg Thieme Verlag Stuttgart - New York.
