23308-82-9

Usage

Uses

Used in Chemical Synthesis:
1-(3-Methoxyphenyl)-ethanol is used as a reactant for the preparation of 2,3-dihydroimidazo[1,2-a]pyridines, which serve as enantioselective acyl transfer catalysts in the kinetic resolution of alcohols. This application is significant for the pharmaceutical industry, as it aids in the synthesis of chiral compounds with high enantiomeric purity.
Used in Oxidation Reactions:
In the field of organic chemistry, 1-(3-Methoxyphenyl)-ethanol is used as a reactant in the chemoselective preparation of aryl aldehydes and ketones. This is achieved through the in situ generated TEMPO-copper(II) diimine catalyzed oxidation of benzylic alcohols in aqueous media. This method is valuable for the synthesis of various organic compounds, including those with potential applications in the pharmaceutical, agrochemical, and materials science industries.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 1-(3-Methoxyphenyl)-ethanol's role as Rivastigmine EP Impurity G suggests that it may have relevance in the pharmaceutical industry, possibly as an intermediate or impurity in the synthesis of Rivastigmine, a drug used for the treatment of Alzheimer's disease and other cognitive disorders. The compound's presence in this context highlights its importance in the development and quality control of pharmaceutical products.

Upstream product

• 917-64-6 methyl magnesium iodide 
• 591-31-1 3-methoxy-benzaldehyde 
• 64-18-6 formic acid 
• 75-89-8 2,2,2-trifluoroethanol 
• 58114-05-9 1-chloro-1-(3'-methoxyphenyl)ethane 
• 32017-77-9 2-(m-methoxyphenyl)oxirane 
• 64-17-5 ethanol 
• 109-86-4 2-methoxy-ethanol 
• 598-38-9 2,2-dicloroethanol 
• 127-09-3 sodium acetate 
• 88563-83-1 1-bromo-1-(3-methoxyphenyl)ethane 
• 64-19-7 acetic acid 
• 109-78-4 3-Hydroxypropionitrile 
• 625-45-6 2-methoxyacetic acid 

Downstream Products

• 58114-05-9 1-chloro-1-(3'-methoxyphenyl)ethane 
• 129052-92-2 N,N-dimethyl-α-(m-methoxyphenyl)ethylamine 
• 586-37-8 1-(3-Methoxyphenyl)ethanone 
• 23308-82-9 S-(-)-1-(3-methoxyphenyl)ethanol 
• 269391-96-0 1-(2-iodo-5-methoxy)-phenylethanol 
• 23308-82-9 (R)-(+)-1-(3-methoxyphenyl)-1-ethanol 
• 605-55-0 phenanthren-2-ol 
• 13837-48-4 2-methoxyphenanthrene 

Relevant academic research and scientific papers

Cinchona-Alkaloid-Derived NNP Ligand for Iridium-Catalyzed Asymmetric Hydrogenation of Ketones

Most ligands applied for asymmetric hydrogenation are synthesized via multistep reactions with expensive chemical reagents. Herein, a series of novel and easily accessed cinchona-alkaloid-based NNP ligands have been developed in two steps. By combining [Ir(COD)Cl]2, 39 ketones including aromatic, heteroaryl, and alkyl ketones have been hydrogenated, all affording valuable chiral alcohols with 96.0-99.9% ee. A plausible reaction mechanism was discussed by NMR, HRMS, and DFT, and an activating model involving trihydride was verified.

Nickel-Catalyzed Enantioselective Hydroboration of Vinylarenes

The enantioselective hydroboration of vinylarenes catalyzed by a chiral, nonracemic nickel catalyst is presented as a facile method for generating chiral benzylic boronate esters. Various vinylarenes react with bis(pinacolato)diboron (B2pin2) in the presence of MeOH as a hydride source to form chiral boronate esters in up to 92% yield with up to 94% ee. The use of anhydrous Me4NF to activate B2pin2 is crucial for ensuring fast transmetalation to achieve high enantioselectivities.

Pincerlike molybdenum complex and preparation method thereof, catalytic composition and application thereof, and alcohol preparation method

The invention discloses a clamp-type molybdenum complex, a preparation method, a corresponding catalyst composition and application. The method comprises the steps: obtaining 9 molybdenum complexes with different structures through coordination reaction of 2-(substituent ethyl)-(5, 6, 7, 8-tetrahydroquinolyl) amine and a corresponding carbonyl molybdenum metal precursor; and catalyzing a ketone compound transfer hydrogenation reaction through a molybdenum complex to generate 40 alcohol compounds. The preparation method of the molybdenum complex is simple, high in yield and good in stability. For a transfer hydrogenation reaction of ketone, the molybdenum-based catalytic system has high catalytic activity and small molybdenum loading capacity, is used for production of aromatic and aliphatic alcohols, and has the advantages of simple method, small environmental pollution and high yield.

Mechanochemical, Water-Assisted Asymmetric Transfer Hydrogenation of Ketones Using Ruthenium Catalyst

Asymmetric catalytic reactions are among the most convenient and environmentally benign methods to obtain optically pure compounds. The aim of this study was to develop a green system for the asymmetric transfer hydrogenation of ketones, applying chiral Ru catalyst in aqueous media and mechanochemical energy transmission. Using a ball mill we have optimized the milling parameters in the transfer hydrogenation of acetophenone followed by reduction of various substituted derivatives. The scope of the method was extended to carbo- and heterocyclic ketones. The scale-up of the developed system was successful, the optically enriched alcohols could be obtained in high yields. The developed mechanochemical system provides TOFs up to 168 h?1. Our present study is the first in which mechanochemically activated enantioselective transfer hydrogenations were carried out, thus, may be a useful guide for the practical synthesis of optically pure chiral secondary alcohols.

Arene-Immobilized Ru(II)/TsDPEN Complexes: Synthesis and Applications to the Asymmetric Transfer Hydrogenation of Ketones

The Noyori-Ikariya (arene)Ru(II)/TsDPEN precatalyst has been anchored to amorphous silica and DAVISIL through the η6-coordinated arene ligand via a straightforward synthesis and the derived systems, (arene)Ru(II)/TsDPEN@silica and (arene)Ru(II)/TsDPEN@DAVISIL, form highly efficient catalysts for the asymmetric transfer hydrogenation of a range of electron-rich and electron-poor aromatic ketones, giving good conversion and excellent ee's under mild reaction conditions. Moreover, catalyst generated in situ immediately prior to addition of substrate and hydrogen donor, by reaction of silica-supported [(arene)RuCl2]2 with (S,S)-TsDPEN, was as efficient as that generated from its preformed counterpart [(arene)Ru{(S,S)-TsDPEN}Cl]@silica. Gratifyingly, the initial TOFs (up to 1085 h?1) and ee's (96–97 %) obtained with these catalysts either rivalled or outperformed those previously reported for catalysts supported by either silica or polymer immobilized through one of the nitrogen atoms of TsDPEN. While the high ee's were also maintained during recycle studies, the conversion dropped steadily over the first three runs due to gradual leaching of the ruthenium.

Phase Separation-Promoted Redox Deracemization of Secondary Alcohols over a Supported Dual Catalysts System

Unification of oxidation and reduction in a one-pot deracemization process has great significance in the preparation of enantioenriched organic molecules. However, the intrinsic mutual deactivation of oxidative and reductive catalysts and the extrinsic incompatible reaction conditions are unavoidable challenges in a single operation. To address these two issues, we develop a supported dual catalysts system to overcome these conflicts from incompatibility to compatibility, resulting in an efficient one-pot redox deracemization of secondary alcohols. During this transformation, the TEMPO species onto the outer surface of silica nanoparticles catalyze the oxidation of racemic alcohols to ketones, and the chiral Rh/diamine species in the nanochannels of the thermoresponsive polymer-coated hollow-shell mesoporous silica enable the asymmetric transfer hydrogenation (ATH) of ketones to chiral alcohols. To demonstrate the general feasibility, a series of orthogonal oxidation/ATH cascade reactions are compared to prove the compatible benefits in the elimination of their deactivations and the balance of the cascade directionality. As presented in this study, this redox deracemization process provides various chiral alcohols with enhanced yields and enantioselectivities relative to those from unsupported dual catalysts systems. Furthermore, the dual catalysts can be recycled continuously, making them an attractive feature in the application.

Supported ionic liquid-like phases as efficient solid ionic solvents for the immobilisation of alcohol dehydrogenases towards the development of stereoselective bioreductions

Polymeric materials containing ionic liquid fragments, like those found in bulk ILs, are excellent solid media for the immobilisation of biocatalysts. Herein, the entrapment of the enzymatic system formed by alcohol dehydrogenase from Rhodococcus ruber (ADH-A) overexpressed in E. coli and its coenzyme has been studied. The activity, stability and reusability of these preparations have been investigated in the bioreduction of prochiral ketones finding excellent levels of conversion and selectivity. Interestingly, the immobilised enzyme remained active and exhibited excellent stability in aqueous solutions after several recycling uses. More importantly, these biopolymer materials retained most of their activity after consecutive reaction cycles, prolonged storage and under flow conditions.

Tridentate nitrogen phosphine ligand containing arylamine NH as well as preparation method and application thereof

The invention discloses a tridentate nitrogen phosphine ligand containing arylamine NH as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The tridentate nitrogen phosphine ligand disclosed by the invention is the first case of tridentate nitrogen phosphine ligand containing not only a quinoline amine structure but also chiral ferrocene at present, a noble metal complex of the type of ligand shows good selectivity and extremely high catalytic activity in an asymmetric hydrogenation reaction, meanwhile, a cheap metal complex of the ligand can also show good selectivity and catalytic activity in the asymmetric hydrogenation reaction, and is very easy to modify in the aspects of electronic effect and space structure, so that the ligand has huge potential application value. A catalyst formed by the ligand and a transition metal complex can be used for catalyzing various reactions, can be used for synthesizing various drugs, and has important industrial application value.

Visible-Light-Driven Catalytic Deracemization of Secondary Alcohols

Deracemization of racemic chiral compounds is an attractive approach in asymmetric synthesis, but its development has been hindered by energetic and kinetic challenges. Here we describe a catalytic deracemization method for secondary benzylic alcohols which are important synthetic intermediates and end products for many industries. Driven by visible light only, this method is based on sequential photochemical dehydrogenation followed by enantioselective thermal hydrogenation. The combination of a heterogeneous dehydrogenation photocatalyst and a chiral molecular hydrogenation catalyst is essential to ensure two distinct pathways for the forward and reverse reactions. These reactions convert a large number of racemic aryl alkyl alcohols into their enantiomerically enriched forms in good yields and enantioselectivities.

Synthesis and catalytic activity of N-heterocyclic silylene (NHSi) iron (II) hydride for hydrosilylation of aldehydes and ketones

A novel silylene supported iron hydride [Si, C]FeH (PMe3)3 (1) was synthesized by C (sp3)-H bond activation with zero-valent iron complex Fe (PMe3)4. Complex 1 was fully characterized by spectroscopic methods and single crystal X-ray diffraction analysis. To the best of our knowledge, 1 is the first example of silylene-based hydrido chelate iron complex produced through activation of the C (sp3)?H bond. It was found that complex 1 exhibited excellent catalytic activity for hydrosilylation of aldehydes and ketones. The catalytic system showed good tolerance and catalytic activity for the substrates with different functional groups on the benzene ring. It is worth mentioning that, the experimental results showed that both ketones and aldehydes could be reduced in good to excellent yields under the same catalytic conditions. Based on the experiments and literature reports, a possible catalytic mechanism was proposed.