129385-10-0

Upstream product

• 35364-99-9 α-chlorobenzyl methyl ether 
• 3481-15-0 benzyl alcohol-d1 
• 74-88-4 methyl iodide 
• 538-86-3 benzyl methyl ether 
• 108-20-3 di-isopropyl ether 
• 82736-93-4 α-deuterated benzaldehyde dimethyl acetal 
• 121235-21-0 bis(1-deuterio-1-methylethyl) ether 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 111-43-3 Dipropyl ether 
• 7021-09-2 rac-methoxyphenylacetic acid 
• 100-52-7 benzaldehyde 

Downstream Products

• 93-58-3 benzoic acid methyl ester 
• 65-85-0 benzoic acid 

Relevant academic research and scientific papers

Boron trifluoride etherate mediated dehydrogenative nucleophilic addition reaction of aliphatic ethers in the presence of acetal affording α,β-unsaturated carbonyl compounds

In the presence of boron trifluoride etherate, some kinds of aliphatic ethers have been found to react with benzaldehyde dimethyl acetal yielding α,β-unsaturated carbonyl compounds with evolution of H2. In this reaction, dehydrogenation of the

Single and double reductive cleavage of C-O bonds of aromatic dimethyl acetals and ketals: Generation of benzylic mono- and dicarbanions

The reductive cleavage of aromatic dimethyl acetals and ketals, 1, with Li metal in THF at low temperature allows the generation of stable α-alkoxy-α-arylsubstituted carbanions, avoiding the Wittig rearrangement. Reaction of these carbanions with various electrophiles afforded the expected products 2. Further in situ reaction of compounds 2 afforded the products of reductive electrophilic disubstitution, 3.

Method for preparing deuterated compound through decarboxylation and deuteration of carboxylic acid

The invention relates to a method for preparing a deuterated compound through decarboxylation and deuteration of carboxylic acid. According to the method, a carboxylic acid compound is used as a raw material, hydrogen atoms of carboxylate radicals are exc

Merging α-Lithiation and Aldol-Tishchenko Reaction to Construct Polyols from Benzyl Ethers

α-Lithiobenzyl ethers, generated by selective α-lithiation, undergo an aldol-Tishchenko reaction upon treatment with carboxylic esters and paraformaldehyde. The reaction of the organolithium with the carboxylate generates an intermediate enolate that, after formaldehyde addition, affords 1,2,3-triol derivatives in a straightforward and one-pot manner. These products are obtained as single diastereoisomers bearing a quaternary stereocenter. The complete diastereocontrol of the aldol-Tishchenko process is attributed to stereoelectronic preferences in the transition state.

Dehydrogenative nucleophilic addition of aliphatic ether to benzaldehyde dimethyl acetal mediated by ether-boron trifluoride (1/1) affording 1-alkoxy-2-alkylindenes or α,β-unsaturated carbonyl compounds specifically

The R2O·BF3-mediated dehydrogenative crossed aldol condensation reaction of acyclic aliphatic ethers with benzaldehyde dimethyl acetal to give specifically indene derivatives or α,β- unsaturated carbonyl compounds has been found. When the ethers have bis(β-alkylethyl) ether structures, dehydrogenative formation of enol ether equivalents followed by successive crossed aldol addition to acetal-originated electrophile and intramolecular electrophilic aromatic substitution reactions give annulation products of 1-alkoxy-2-alkylindenes. When the ether has two β- and one or more α-hydrogens, α,β-unsaturated carbonyl compounds are obtained. The structural correlation between deuterated starting materials and the obtained products, the structural requirements for ethers, and the distinct substrate specificity have revealed the reaction routes and mechanisms.

Metalation of arylmethyl alkyl ethers

Arylmethyl alkyl ethers 1a-11 were metallated with n-BuLi or sec-BuLi in THF at different temperatures, affording α-alkoxy-substituted arylmethyllithium derivatives. At low temperature, the organometallics derived from methyl and isopropyl ethers are suff

The Mechanism of RuO4-Mediated Oxidations of Ethers: Isotope Effects, Solvent Effects and Substituent Effects

The mechanism of the RuO4-mediated oxidation of ethers to esters has been investigated.Oxidation of cyclopropylmethyl methyl ether gave methyl cyclopropanecarboxylate.No rearranged products were observed.On RuO4 oxidation of benzyl methyl ether and p-methoxybenzyl methyl ether in CCl4 with NaIO4 as stoichiometric oxidant, no chlorinated products were observed.A series of 4-substituted benzyl methyl ethers was oxidized with RuO4-NaIO4.A correlation of the rate of the reaction with Hammett ?-values gave a ρ of -1.7, indicating only a moderate charge separation in the transition state (TS).Benzyl methyl ether (1) was oxidized in a series of acetone-water mixtures.From these experiments, a Grunwald-Winstein m-value of 0.11 was obtained, indicating a non-polar TS for the reaction.PhCHDOCH3 (2) and PhCD2OCH3 (3) were oxidized and two deuterium isotipe effects, one of 6.1+/-0.4 and another of 1.3+/-0.1 were obtained.If one assumes a one-step reaction mechanism, the value of 1.3 would be a large α-secondary isotope effect, indicating a change in the hybridization of the benzylic carbon during the reaction. α-Methylbenzyl methyl ether (4) was oxidized at a seventh of the rate of 1, despite the fact that 4 would have given a more stable carbocation than 1.These conflicting pieces of evidence are difficult to rationalise with a hydride or hydrogen abstraction mechanism.Instead it is proposed that the reaction proceeds by either a concerted reaction or by a reversible oxidative addition of the ether to RuO4 followed by a slow concerted step to give the product.

Substitutions and dehydrogenations by 2,2-bis(trifluoromethyl)-ethylene-1,1-dicarbonitrile via hydride abstraction

Substitution of benzylic H by the title compound (BTF) gives rise to products with -CH(CF3)2 terminus exclusively; an intermediate benzylic ion pair results from hydride transfer. Instead of ion recombination, proton transfer may be the concluding step generating dehydrogenation products and 2,2-bis(trifluoromethyl)ethane-1,1-dicarbonitrile.