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Upstream product

• 13608-28-1 4,4-dimethyl-2-(2-phenylethyl)-4,5-dihydro-1,3-oxazole 
• 78-92-2 iso-butanol 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 501-52-0 3-Phenylpropionic acid 
• 104-55-2 3-phenyl-propenal 
• 107978-04-1 3-(1-oxo-3-phenylpropyl)-1,3-oxazolidin-2-one 
• 104-53-0 3-phenyl-propionaldehyde 
• 100-44-7 benzyl chloride 
• 645-45-4 hydrocinnamic acid chloride 
• 22767-96-0 Benzyl 3-phenylpropionate 
• 2021-28-5 ethyl dihydrocinnamate 
• 65439-56-7 3-phenyl-1-(2-thioxothiazolidin-3-yl)propan-1-one 

Relevant academic research and scientific papers

Imidazolium Based Fluorous N-Heterocyclic Carbenes as Effective and Recyclable Organocatalysts for Redox Esterification

A series of new highly fluorophilic ionic liquids (f > 110) was synthetized from 3-iodopropyltris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane and N-alkyl imidazoles, followed by anion exchange. N-heterocyclic carbenes generated in situ from obtained imidazolium salts were employed to catalyze redox esterification (umpolung) of cinnamaldehyde with alcohols. The most effective N-methyl derivative with iodide as a counter anion was studied in detail with respect to the optimization of reaction conditions, substrate scope and recyclability. Recovery of the precatalyst was achieved using either fluorous extraction or performing the reaction in suitable fluorous biphase system with direct recycling of the fluorinated precatalyst phase. For both tested options, the catalytic activity did not significantly decrease within 5 subsequent cycles. The redox esterification was shown to proceed also in supercritical carbon dioxide (scCO2) as an alternative solvent where the activity of the fluorinated catalyst was also superior to the nonfluorinated model, while retaining the benefit of easy recycling.

Broadly Applicable Ytterbium-Catalyzed Esterification, Hydrolysis, and Amidation of Imides

An efficient, broadly applicable, operationally simple, and divergent process for the transformation of imides into a range of carboxylic acid derivatives under mild conditions is reported. By simply using catalytic amounts of ytterbium(III) triflate as a Lewis acid promoter in the presence of alcohols, water, amines, or N,O-dimethylhydroxylamine, a broad range of imides is smoothly and readily converted to the corresponding esters, carboxylic acids, amides, and Weinreb amides in good yields. This method notably enables an easy cleavage of oxazolidinone-based auxiliaries.

Ambulation of Incipient Proton during Gas-Phase Dissociation of Protonated Alkyl Dihydrocinnamates

Upon activation in the gas phase, protonated alkyl dihydrocinnamates undergo an alcohol loss. However, the mechanism followed is not a simple removal of an alkanol molecule after a protonation on the alkoxy group. The mass spectrum of the m/z 166 ion for deuteron-charged methyl dihydrocinnamate showed two peaks of 1:5 intensity ratio at m/z 133 and 134 to confirm that the incipient proton is mobile. The proton initially attached to the carbonyl group migrates to the ring and randomizes before a subsequent transfer of one of the ring protons to the alkoxy group for the concomitant alcohol elimination. Moreover, protonated methyl dihydrocinnamate undergoes more than one H/D exchange. The spectra recorded from m/z 167 and 168 ions obtained for di- and tri-deuterio isotopologues showed peak pairs at m/z 134, 135 and 135, 136, at 1:2 and 1:1 intensity ratios, respectively, confirming the benzenium ion intermediate achieves complete randomization before the proton transfer. Additionally, protonated higher esters of alkyl dihydrocinnamates undergo a cleavage of the O-CH2 bond to form an ion/neutral complex, which, upon activation, dissociates generating a carbenium ion and dihydrocinnamic acid, or rearranges to generate protonated dihydrocinnamic acid and an alkene by a nonspecific proton transfer.

Pd-catalyzed aldehyde to ester conversion: A hydrogen transfer approach

Aliphatic and aromatic aldehydes are successfully converted into their corresponding esters using Pd(OAc)2 and XPhos. This approach utilizes a hydrogen transfer protocol: concomitant reduction of acetone to isopropanol provides an inexpensive and sustainable approach that mitigates the need for other oxidants.

One-pot sequential synthesis of ethers from an aliphatic carboxylic acid and an alcohol by indium-catalyzed deoxygenation of an ester

We have developed a widely applicable and direct method of etherification from a carboxylic acid and an alcohol by indium-catalyzed deoxygenation of the transient ester formed in a one-pot reaction. This simple catalytic reducing system appears to be remarkably tolerant of several functional groups including alkenes, halogens, nitro and heterocyclic groups. A reducing system composed of InBr3 and an economical hydrosiloxane, PMHS (polymethylhydrosiloxane) , enabled one-pot etherification by using a variety of aliphatic carboxylic acids and alcohols. Copyright

Fluoroalkyldistannoxane Catalysts for Transesterification in Fluorous Biphase Technology

Novel, practical protocols of transesterification have been advanced with recourse to fluorous biphase technology. The fluoroalkyldistannoxane catalysts enable transesterification in FC-72 solvent to furnish 100% yields of the desired esters by use of reactants ester and alcohol in a 1:1 ratio. The catalysts also work in FC-72/organic solvent system as well as in toluene alone. A number of esters and alcohols bearing various functional groups are employable. The catalysts can be totally recovered and reused. More conveniently, the catalyst solution in FC-72 which is separated from the reaction mixture is directly used for the next reaction.

A practical and green chemical process: Fluoroalkyldistannoxane-catalyzed biphasic transesterification

There is no need for the recovery of the catalyst in the fluorous biphasic transesterification catalyzed by [{Cl(C6F13CH2CH2)2 SnOSn(C6F13CH2CH2) 2Cl}2] (1; see scheme), which results in quantitative conversions and yields. An FC-72 solution of the dimeric flouroalkyldistannoxane 1 can be recycled repeatedly without having to recover the neat catalyst.

Efficient acylation of alcohols with acylthiazolidine-2-thiones and cesium fluoride

Primary alcohols are acylated in good yield under almost neutral conditions with 3-acylthiazolidine-2-thiones and cesium fluoride.For secondary alcohols, the yield is improved by the addition of zinc bromide. t-Butanol is not acylated.