82529-79-1

Upstream product

• 60-12-8 2-phenylethanol 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 824-94-2 p-methoxybenzyl chloride 
• 350848-02-1 2-[(4-methoxybenzyl)oxy]-3-nitropyridine 
• 2746-25-0 p-Methoxybenzyl bromide 
• 105-13-5 4-Methoxybenzyl alcohol 
• 866124-70-1 p-methoxybenzyloxydiphenylphosphine 
• 127866-65-3 5-[(4-methoxybenzyl)sulfanyl]-1-phenyl-1H-tetrazole 
• 100-44-7 benzyl chloride 
• 103-45-7 acetic acid phenethyl ester 

Downstream Products

• 60-12-8 2-phenylethanol 
• 54673-12-0 (2-(methoxymethoxy)ethyl)benzene 
• 101746-67-2 bis(2-phenylethyloxy)methane 
• 123-11-5 4-methoxy-benzaldehyde 
• 83318-92-7 ethyl p-methoxybenzyl sulfide 

Relevant academic research and scientific papers

Zirconium-catalysed direct substitution of alcohols: enhancing the selectivity by kinetic analysis

Kinetic analysis was used as a tool for rational optimization of a catalytic, direct substitution of alcohols to enable the selective formation of unsymmetrical ethers, thioethers, and Friedel-Crafts alkylation products using a moisture-tolerant and commercially available zirconium complex (2 to 8 mol%). Operating in air and in the absence of dehydration techniques, the protocol furnished a variety of products in high yields, including glycosylated alcohols and sterically hindered ethers. In addition, the kinetic studies provided mechanistic insight into the network of parallel transformations that take place in the reaction, and helped to elucidate the nature of the operating catalyst.

Direct and efficient synthesis of unsymmetrical ethers from alcohols catalyzed by Fe(HSO4)3 under solvent-free conditions

Highly efficient Fe(HSO4)3 catalyzed etherification of primary, secondary and tertiary benzylic alcohols with primary and secondary aliphatic alcohols is reported. The reaction affords unsymmetrical benzyl ethers in good to excellent yields under solvent-free conditions.

A gold catalytic the method for synthesizing calls the ether

The invention provides a synthetic method of asymmetrical ether in the field of organic synthesis. The general equation of reaction is defined in the specification. In the equation, R-OH is benzyl alcohol, p-methoxy benzyl alcohol, tert-butyl alcohol, diphenyl carbinol or triphenylmethanol; and R'OH is common alkyl alcohol or a compound containing hydroxyl groups. A gold catalyst required by the reaction is Ph3PAuCl, Ph3PAuNTf2, HAuCl4, NaAuCl4, Ph3PAuOTf, Ph3PAuSbF6, IPrAuCl or nano-gold. A medium required by the reaction is solvent-free, and is toluene, mesitylene, 1,2-dichloroethane, tetrahydrofuran, acetonitrile or acetone. The reaction is implemented by heating through a microwave reactor. The method has advantages as follows: raw materials are easily available; operation is simple; the range of application is wide; atom economy is good; and the reaction is green.

Gold(I)-catalyzed synthesis of unsymmetrical ethers using alcohols as alkylating reagents

A microwave-irradiated alcohol-protecting strategy based on gold catalysis utilizing benzyl alcohol, tert-butyl alcohol and triphenylmethanol as alkylating reagents has been developed. This protecting strategy has wide functional group tolerance with satisfactory yields for the majority of the selected alcohols. The mechanism of this transformation was probed with oxygen-18 isotope labelled alcohols assisted by GC-MS techniques and chemical kinetic experiments. This strategy provides an efficient, straightforward and alternative approach to the preparation of benzyl, tert-butyl and trityl ethers in organic synthesis.

METHOD OF PRODUCING VINYLBENZYL(FLUOROALKYL) ETHER

PROBLEM TO BE SOLVED: To provide a method of producing a vinylbenzyl(fluoroalkyl) ether industrially at low costs. SOLUTION: A method of producing a vinylbenzyl(fluoroalkyl) ether of formula (1) (in the formula, Rf is a fluoroalkyl group, and n is an integer of 1-3) comprises reacting a fluoroalkyl alcohol of formula (2) (in the formula, Rf is a fluoroalkyl group, and n is an integer of 1-3) with chloromethylstyrene in a solvent selected from tertiary alcohols, nitrogen-containing organic solvents and sulfur-containing organic solvents in the presence of a solid alkali. COPYRIGHT: (C)2015,JPOandINPIT

Step-economy etherification of acylated alcohols

An efficient and convenient protocol has been developed for ether bond formation in mild conditions. A mixture of primary/secondary ester and allylic/benzylic halide in tetrahydrofuran was treated with KOtBu at room temperature to give ether in high yield. This step economic method enabled direct alkylation of the acyl group masked O-nucleophiles. Application of this method in carbohydrate synthesis was feasible and chemo-selectivity can be achieved.

A convenient approach for the deprotection and scavenging of the PMB group using POCl3

A convenient and high yielding approach for the deprotection and scavenging of the p-methoxybenzyl (PMB) group in PMB ethers and PMB esters was developed using POCl3 as the reagent. 4-Methoxybenzyl chloride, a starting material used for the preparation of PMB ethers and esters was regenerated in the deprotection step. This mild and selective procedure tolerates several acid sensitive functional groups. The Royal Society of Chemistry 2013.

Benzylation of hydroxy groups with tertiary amine as a base

The benzylation of hydroxy groups in the presence of tertiary amines is described. A mixture of an alcohol and a benzyl halide afforded the corresponding benzyl ether in good to excellent yields in the presence of diisopropylethylamine. The importance of solventless conditions was observed. The reaction showed high tolerance to many functional groups including benzoate, even at a reaction temperature of 150 °C. Sodium iodide was found to be an efficient catalyst to accelerate the reaction.

Suzuki coupling of potassium cyclopropyl- and alkoxymethyltrifluoroborates with benzyl chlorides

Efficient Csp3-Csp3 Suzuki couplings have been developed with both potassium cyclopropyl- and alkoxymethyltrifluoroborates. Moderate to good yields have been achieved in the cross-coupling of potassium cyclopropyltrifluoroborate with benzyl chlorides possessing electron-donating or electron-withdrawing substituents. Benzyl chloride was also successfully cross-coupled to potassium alkoxymethyltrifluoroborates derived from primary, secondary, and tertiary alcohols.

A mild method for the protection of alcohols using a para-methoxybenzylthio tetrazole (PMB-ST) under dual acid-base activation

With a view to expand the repertoire of chemoselective methods applicable to sensitive and multifunctional substrates, the p-methoxybenzylation of alcohols under essentially neutral conditions is reported. This was achieved by the silver triflate (AgOTf) activation of 5-(p-methoxybenzylthio)-1-phenyl-1H-tetrazole (PMB-ST) in the presence of 2,6-di-tert-butyl-4-methylpyridine (DTBMP).