61812-55-3

Upstream product

• 13871-89-1 trimethylsilyl cyclohexyl ether 
• 98-86-2 acetophenone 
• 98-85-1 1-Phenylethanol 
• 108-93-0 cyclohexanol 
• 100-42-5 styrene 
• 799254-89-0 (S)-1-phensylethyl diphenykphosphinate 
• 98-89-5 Cyclohexanecarboxylic acid 
• 93-96-9 bis(1-phenylethyl)ether 
• 110-82-7 cyclohexane 
• 100-41-4 ethylbenzene 

Relevant academic research and scientific papers

Hindered dialkyl ether synthesis with electrogenerated carbocations

Hindered ethers are of high value for various applications; however, they remain an underexplored area of chemical space because they are difficult to synthesize via conventional reactions1,2. Such motifs are highly coveted in medicinal chemistry, because extensive substitution about the ether bond prevents unwanted metabolic processes that can lead to rapid degradation in vivo. Here we report a simple route towards the synthesis of hindered ethers, in which electrochemical oxidation is used to liberate high-energy carbocations from simple carboxylic acids. These reactive carbocation intermediates, which are generated with low electrochemical potentials, capture an alcohol donor under non-acidic conditions; this enables the formation of a range of ethers (more than 80 have been prepared here) that would otherwise be difficult to access. The carbocations can also be intercepted by simple nucleophiles, leading to the formation of hindered alcohols and even alkyl fluorides. This method was evaluated for its ability to circumvent the synthetic bottlenecks encountered in the preparation of 12 chemical scaffolds, leading to higher yields of the required products, in addition to substantial reductions in the number of steps and the amount of labour required to prepare them. The use of molecular probes and the results of kinetic studies support the proposed mechanism and the role of additives under the conditions examined. The reaction manifold that we report here demonstrates the power of electrochemistry to access highly reactive intermediates under mild conditions and, in turn, the substantial improvements in efficiency that can be achieved with these otherwise-inaccessible intermediates.

W-Ti-O mixed metal oxide catalyzed dehydrative cross-etherification of alcohols

A dehydrative cross-etherification reaction of two different alcohols is achieved in the presence of hydrothermally synthesized tungsten-titanium mixed metal oxide (W-Ti-O) catalyst. The reaction is environmentally benign: organic solvent is not necessary and the catalyst is readily recovered and reusable.

Ether Synthesis through Reductive Cross-Coupling of Ketones with Alcohols Using Me 2 SiHCl as both Reductant and Lewis Acid

We report that a Lewis acidic silane, Me 2 SiHCl, can mediate the direct cross-coupling of a wide range of carbonyl compounds with alcohols to form dialkyl ethers. The reaction is operationally simple, tolerates a range of polar functional groups, can be utilized to make sterically hindered ethers, and is extendable to sulfur and nitrogen nucleophiles.

CATALYTIC C-H BOND ACTIVATION FOR THE SYNTHESIS OF ETHERS AND THIOETHERS

Disclosed is a method for the transition metal-mediated oxidation of C-H bonds to form C-0 or C-S bonds. The methods are useful for the formation of ethers (R-OR') from alcohols, R'OH, and sp3 -hybridized C-H bonds in substrates, R-H. Aryl or heteroaryl acetates may also be used for C-H to C-OAr bond formation. The methods are also useful in the preparation of C-S bonds from acetyl-protected thiols, MeC(0)SR, and disulfides, RSSR. Advantageously, the methods minimize reaction steps, the handling of oxidized intermediates, and environmental impact.

A simple and an efficient indium trichloride catalyzed benzyl etherification

An efficient method has been developed for the synthesis of benzyl ethers of alkyl, allyl and propargyl alchols by simple, direct coupling of alcohols in the presence of catalytic amount of L1C13 under solvent-free condition.

An efficient method for the ether forming reaction between alkyl diphenylphosphinate and alkoxytrimethylsilane by the promotion of trimethylsilyl triflate

The trimethylsilyl triflate promoted reactions of alkyl diphenylphosphinates with alkoxytrimethylsilanes in chloroform, 1,2-dichloroethane or 1,2-dichloropropane, proceeded smoothly to give the corresponding ethers in good yields.

Vapor pressures and enthalpies of vaporization of benzyl halides and benzyl ethers

Molar enthalpies of vaporization ΔlgHmo of seven benzyl halides and seven benzyl ethers have been obtained from the temperature dependence of the vapor pressure measured by the transpiration method. These values and the correlation-gas chromatography method, based on Kovat's index, have been applied for the determination of ΔlgHmo of three cumyl halides (Cl, Br, and I). The data obtained for ΔlgHmo of benzyl derivatives have been checked successfully for internal consistency using enthalpies of formation of alkyl halides and alkyl ethers available from the literature.

Chemical equilibrium study in the reacting system of (1-alkoxyethyl)benzene synthesis from isoalkanols and styrene

The chemical equilibrium of the reactive systems isoalkanol + styrene ? (1-alkoxyethyl)benzene (alkyl is isopropyl, sec-butyl, and cyclohexyl) was studied in the liquid phase in the temperature range 343 to 433 K using a cation exchanger as heterogeneous

BiBr3, an efficient catalyst for the benzylation of alcohols: 2-Phenyl- 2-propyl, a new benzyl-type protecting group

The benzylation of aliphatic alcohols with various benzylic alcohols has been achieved in the presence of BiBr3 under mild conditions. 2- Phenylpropan-2-ol proved to be the most efficient and can be considered as a novel protecting group. (C) 2000 Elsevier Science Ltd.

Efficient reductive etherification of carbonyl compounds with alkoxytrimethylsilanes

An efficient TMSOTf catalyzed ether synthesis from carbonyl compounds and alkoxytrimethylsilanes via triethylsilane-reduction is described.