113386-12-2

Upstream product

• 620-02-0 5-Methylfurfural 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 534-22-5 2-methylfuran 
• 2746-25-0 p-Methoxybenzyl bromide 
• 824-94-2 p-methoxybenzyl chloride 
• 105-13-5 4-Methoxybenzyl alcohol 
• 356552-15-3 (4-methoxyphenyl)(5-methylfuran-2-yl)methanol 

Relevant academic research and scientific papers

Gold-catalyzed etherification and friedel - Crafts alkylation using ortho-alkynylbenzoic acid alkyl ester as an efficient alkylating agent

A gold-catalyzed alkylation of alcohols and aromatic compounds is described. The reaction of ortho-alkynylbenzoic acid alkyl esters with alcohols or aromatic compounds occurs in the presence of catalytic amounts of Ph 3PAuCl and AgOTf under mild conditions to produce corresponding ethers or Friedel-Crafts alkylation products in good to high yields. The reaction likely proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack of alcohols or aromatic compounds.

CHEMICALLY STABLE LIGNIN DERIVATIVE AND METHOD FOR PREPARING SAME

A lignin derivative including a unit of general formula (I): in which R1, R2, R3 and R4, which may be identical or different, each represent a hydrogen atom, a methoxy group —OMe, a hydroxyl group, where appropriate protected by a protective group of a hydroxyl function, or a unit R5 represents a hydrogen atom, a protective group of a hydroxyl function or a unit; A represents an oxygen atom, a sulfur atom, an —NH group or an —NR′ group; and R′1, R′2, R′3 and R′4 each represent a hydrogen atom or a substituent not including a mesomeric-effect electron-withdrawing group conjugated to the aromatic ring, a substituent from R′1, R′2, R′3 and R′4 representing the covalent bond with the benzylic carbon.

Catalytic Formal Benzylic C-H Bond Functionalization of 2,5-Dialkylfuran Derivatives with Ferrocenyl Alcohols as Alkylation Reagents

The inert benzylic C-H bond of π-electron-rich heteroaromatic 2,5-dialkylfuran derivatives was conveniently functionalized with ferrocenyl alcohols as alkylation reagents under catalytic acidic conditions at room temperature, which features chemo- and reg

A two-phase system for the clean and high yield synthesis of furylmethane derivatives over -SO3H functionalized ionic liquids

A new and effective unique two-phase reaction system is investigated for the high yield production of tri(furyl)methane from furfural and furan. This strategy includes the use of an acidic aqueous phase (water + -SO3H functionalized IL) and furan phase, which significantly suppresses polymer formation, thereby increasing the yield of tri(furyl)methane. Furan serves as a reactant as well as an extraction solvent for the recovery of the condensation products. For comparison, different -SO3H functionalized ionic liquids are prepared and their performances evaluated for the condensation of furan and furfural. The ionic liquids with alkyl chain linkers are found to be more effective and acidic than those with imidazolium linked N-sulfonic acids. In addition, an increase in carbon chain length between imidazole/tri-ethylamine/pyridine and -SO3H, increases the catalytic activity of the respective ionic liquids. Among the several prepared ionic liquids, the strongly acidic imidazolium based butylsulfonic acid 6 shows the best activity with a maximum condensation product yield of 84%. This strategy offers a significantly high yield of the condensation products of furan and furfural compared to the traditional mineral acid route. The activity and stability of the -SO3H functionalized 6 is confirmed from seven successful recycles, in which there is no reduction in its activity. Finally, this new strategy is successfully extended for the condensation of furan derivatives (e.g. furan and 2-methylfuran) with several different aldehydes, ketones and alcohols.

Solvent-free Br?nsted acid catalysed alkylation of arenes and heteroarenes with benzylic alcohols

A simple and efficient alkylation of aromatic and heteroaromatic compounds via the direct SN1-type nucleophilic substitution of benzylic alcohols in the presence of catalytic amounts of the strong Br?nsted acid o-benzenedisulfonimide under neat conditions is herein reported. A library of di- and triaryl (and heteroaryl) methanes was prepared in good yields and high regioselectivity. The observed reactivity was shown to be in agreement with Mayr's nucleophilicity and electrophilicity scales.

Organocatalyzed Friedel-Crafts arylation of benzylic alcohols

Electron-rich aromatic and heteroaromatic rings are functionalized directly with a variety of benzylic alcohols under mild conditions. The reaction is catalyzed by commercially available pentafluorophenylboronic acid, which is stable under ambient conditions and recoverable. The reaction itself is highly atom economical and produces water as the only byproduct. A Friedel-Crafts mechanism is proposed.

Gold-catalyzed substitution reaction with ortho-alkynylbenzoic acid alkyl ester as an efficient alkylating agent

ortho-Alkynylbenzoic acid alkyl esters behave as alkylating agents in combination with gold catalysts. The reaction with alcohols occurs smoothly in the presence of catalytic amounts of Ph3PAuCl and AgOTf under mild conditions to produce the corresponding ether products in high yields. The protocol is also useful for Friedel-Crafts alkylation and N-alkylation of sulfonamides. The reaction likely proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack of nucleophiles, such as alcohols, aromatic compounds, and sulfonamides.

METHOD FOR ESTABLISHING CC BONDS BETWEEN ELECTROPHILIC SUBSTRATES AND ? - NUCLEOPHILES IN NEUTRAL TO ALKALINE AQUEOUS OR ALCOHOLIC SOLVENTS WITHOUT USING A LEWIS OR BRONSTED ACID

The invention relates to a method for establishing carbon-carbon bonds by reacting electropohilic substrates that have a solvolysis rate kEtOH (25°C) > 10-6 s-1 and ? compounds. The method is characterized by generating the intermediary carbocations in neutral to alkaline aqueous or alcoholic solvents or solvent mixtures without using a Lewis or Br?nsted acid.

Electrophilic alkylations in neutral aqueous or alcoholic solutions

Acid-free Friedel-Crafts chemistry: A paradox? Nucleophilicity scales, based on reactions with benzhydrylium ions, show that many π systems are more nucleophilic than aqueous or alcoholic solutions that are generally employed as solvents for SN1 reactions. Solvolytically generated carbocations can, therefore, be trapped by donor-substituted arenes and alkenes to form products of Friedel-Crafts-type reactions in neutral aqueous solutions (see scheme).