67233-95-8

Upstream product

• 66821-19-0 1-(1'-ethoxyvinyl)-4-methoxybenzene 
• 100-66-3 methoxybenzene 
• 123-63-7 paracetaldehyde 
• 64-17-5 ethanol 
• 75-89-8 2,2,2-trifluoroethanol 
• 58287-11-9 1-(4-methoxyphenyl)ethyl 4-nitrobenzoate 
• 3319-15-1 rac-1-(4-methoxyphenyl)-ethanol 
• 88563-46-6 1-(p-methoxyphenyl)ethyl phenyl ether 
• 18207-33-5 1-(4-methoxyphenyl)ethyl carbocation 
• 94670-31-2 1-(4-methoxyphenyl)ethyl trifluoroethyl ether 
• 105-57-7 diethyl acetal 
• 637-69-4 4-Methoxystyrene 
• 1258980-78-7 (R)-N-but-3-enyl-N-(α-methyl-p-methoxybenzyl)amine 
• 1273232-31-7 tert-butyl (2R,3S,4S,5R,αR)-2-hydroxy-3-[N-but-3'-enyl-N-(α-methyl-p-methoxybenzyl)amino]-4,5-O-isopropylidenehept-6-enoate 

Downstream Products

• 64-17-5 ethanol 
• 94670-31-2 1-(4-methoxyphenyl)ethyl trifluoroethyl ether 
• 4356-69-8 1,1-bis-(4-methoxyphenyl)ethylene 
• 3319-15-1 rac-1-(4-methoxyphenyl)-ethanol 

Relevant academic research and scientific papers

Chemoenzymatic intermolecular haloether synthesis

A chemoenzymatic method for the synthesis of haloethers is presented. A combination of enzymatic hypohalite synthesis with spontaneous oxidation of alkenes and nucleophilic attack by various alcohols enabled the synthesis of a wide range of haloethers. The reaction system has been characterised and current imitations have been worked out. In the present, aqueous reaction system, hydroxyhalide formation represents the main undesired side reaction. Nevertheless, semi-preparative scale synthesis of a range of haloethers is demonstrated.

Iodine-catalyzed transformation of aryl-substituted alcohols under solvent-free and highly concentrated reaction conditions

Iodine-catalyzed transformations of alcohols under solvent-free reaction conditions (SFRC) and under highly concentrated reaction conditions (HCRC) in the presence of various solvents were studied in order to gain insight into the behavior of the reaction intermediates under these conditions. Dimerization, dehydration and substitution were the three types of transformations observed with benzylic alcohols. Dimerization and substitution reactions were predominant in the case of primary- and secondary alcohols, whereas dehydration prevailed in the case of tertiary alcohols. The relative reactivity of substituted 1-phenylethanols in I2-catalyzed dimerization under SFRC provided a good Hammett plot ρ+ = -2.8 (r2 = 0.98), suggesting the presence of electron-deficient intermediates with a certain degree of developed charge in the rate-determining step.

Direct synthesis of ethers from aldehydes and ketones. One-pot reductive etherification of benzaldehydes, alkyl aryl ketones, and benzophenones

Benzyl alcohols formed by the reduction of benzaldehydes, alkyl aryl ketones, and benzophenones with sodium tetrahydridoborate in alcohols undergo in situ etherification with the solvent in the presence of a catalytic amount of HCl. Thus the process may be regarded as one-pot transformation of carbonyl compounds into the corresponding benzyl ethers. The yields of ethers depend on the substituent nature in the aromatic fragment of the initial carbonyl compound and on the alcohol used as reduction medium.

Hydrochloric acid as an efficient catalyst for intermolecular condensation of alcohols. A simple and highly efficient synthesis of unsymmetrical ethers from benzylic alcohols and alkanols

Benzylic alcohols and diarylmethanols with electron-donating substituents in the aromatic ring reacted with aliphatic alcohols in the presence of a catalytic amount of HCl to give the corresponding alkyl arylmethyl ethers. The reactivity of diarylmethanols in the intermolecular dehydration depended on the nature of substituents in the aromatic rings and structure of aliphatic alcohol.

Selective catalytic synthesis of unsymmetrical ethers from the dehydrative etherification of two different alcohols

The cationic ruthenium-hydride complex [(C6H6)(PCy3)(CO)RuH]+BF4- catalyzes selective etherification of two different alcohols to form unsymmetrically substituted ethers. The catalytic method exhibits a broad substrate scope while tolerating a range of heteroatom functional groups in forming unsymmetrical ethers, and it is successfully used to directly synthesize a number of highly functionalized chiral nonracemic ethers.

Asymmetric synthesis of the tropane alkaloid (+)-pseudococaine via ring-closing iodoamination

Ring-closing iodoamination of tert-butyl 2-hydroxy-7-[N-methyl-N-(α- methyl-p-methoxybenzyl)amino]cyclohept-3-ene-1-carboxylates proceeds with concomitant loss of the N-α-methyl-p-methoxybenzyl group to give the corresponding 8-azabicyclo[3.2.1]octane sca

Feeding the Heck reaction with alcohol: One-pot synthesis of stilbenes from aryl alcohols and bromides

Aryl alcohols are employed as feedstock for the Heck reaction. Keggin-type heteropolyacids catalyse the selective dehydration of the alcohols to styrenes, which, in one-pot, undergo palladium-catalysed Heck arylation with aryl bromides, affording broadly functionalised stilbenes. The choice of solvent is critical for the cascade dehydration-Heck reaction, with electron-rich aryl alcohols preferring a basic medium while electron-deficient ones demanding solvents of lower basicity. Copyright

Asymmetric synthesis of polyhydroxylated pyrrolizidines via transannular iodoamination with concomitant N-debenzylation

The doubly diastereoselective "matched" conjugate addition of lithium (R)-N-but-3-enyl-N-(α-methyl-p-methoxybenzyl)amide to tert-butyl (4S,5R,E)-4,5-O-isopropylidene-2,7-dienoate (derived from d-ribose in 3 steps) and in situ enolate oxidation with (-)-camphorsulfonyloxaziridine was followed by ring-closing metathesis with Grubbs I to give a hexahydroazocine scaffold. Subsequent treatment with I2 resulted in transannular iodoamination accompanied by loss of the α-methyl-p-methoxybenzyl group to give the corresponding pyrrolizidine scaffold as a single diastereoisomer upon direct crystallization from the crude reaction mixture. Further functional group manipulations enabled the preparation of (-)-7a-epi-hyacinthacine A1.

Silica-supported KHSO4: An efficient system for activation of aromatic terminal olefins

Potassium hydrogen sulfate adsorbed on chromatography-grade silica gel activates electron-rich aromatic terminal olefins towards nucleophilic attack at the benzylic position by alcohols. Temperature plays a crucial role and facilitates suppressing nucleophilic reaction in favor of dimerization of the terminal olefin. Georg Thieme Verlag Stuttgart - New York.

Bifunctional copper catalysts for an atom efficient ether synthesis

A direct etherification of aromatic ketones and aliphatic alcohols into the corresponding asymmetrical ethers by the use of a bifunctional heterogeneous copper catalyst is described. The reaction protocol reveals to be versatile and convenient respect to the traditional ether synthesis for both environmental and practical concerns.