22733-94-4

Usage

InChI:InChI=1/C14H18O2/c15-14(13-9-5-2-6-10-13)16-11-12-7-3-1-4-8-12/h1,3-4,7-8,13H,2,5-6,9-11H2

Upstream product

• 501-53-1 benzyl chloroformate 
• 98-89-5 Cyclohexanecarboxylic acid 
• 4630-82-4 methyl cyclohexylcarboxylate 
• 100-51-6 benzyl alcohol 
• 221887-36-1 2,2,2-tribromoethyl cyclohexanecarboxylate 
• 1977-87-3 cyclohexanecarbonyl fluoride 
• 31139-36-3 dibenzyl dicarbonate 
• 34899-90-6 1-bromocyclohexanecarbaldehyde 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 108-88-3 toluene 
• 141-53-7 sodium formate 
• 110-83-8 cyclohexene 
• 530-48-3 1,1-Diphenylethylene 
• 110-82-7 cyclohexane 

Downstream Products

• 181235-21-2 1-tert-Butoxycarbonylmethyl-cyclohexanecarboxylic acid benzyl ester 

Relevant academic research and scientific papers

Iron(III)-zirconium(IV) combined salt immobilized on N-(polystyrylbutyl) pyridinium triflylimide as a reusable catalyst for a dehydrative esterification reaction

N-(Polystyrylbutyl)pyridinium triflylimide is prepared by a coupling reaction of commercially available 4-bromobutyl-polystyrene with pyridine and a subsequent anion exchange reaction with lithium triflylimide. This new polystyrene-bound pyridinium salt is useful as a solid support to immobilize a zirconium(IV)-iron(III) binary metal complex, which is a homogeneous catalyst for the dehydrative ester condensation of an equimolar mixture of carboxylic acids and alcohols. The immobilized zirconium(IV)-iron(III) complex is easily recovered by filtration after complete esterification, and is reusable without any loss of activity.

Solar and visible-light active nano Ni/g-C3N4photocatalyst for carbon monoxide (CO) and ligand-free carbonylation reactions

In this study, we investigate the amino and alkoxycarbonylation reaction between various substituted aryl halides, benzyl iodides, and iodocyclohexane with different types of amines and alcohols in the absence of carbon monoxide gas and ligands. Similar reactions are carried out at high temperatures, in the presence of appropriate ligands, stoichiometric amounts of bases, and gaseous carbon monoxide, which endanger the health of organic chemists. We present a novel method that does not utilize ligands, bases, gaseous CO, and special conditions. This procedure is a redox reaction carried out by new economic nano Ni/g-C3N4at room temperature and under visible light. Mo(CO)6was used toin situgenerate CO, to resolve the problems caused by the use of CO gas. This protocol has the ability to be used on a gram scale by using a continuous flow reactor.

Epoxide as precatalyst for metal-free catalytic transesterification

Transesterification of methyl esters was accelerated by an in situ-generated metal-free catalyst comprising a quaternary alkylammonium salt and an epoxide. The combination of a quaternary alkylammonium acetate and glycidol is optimal, and various esters were synthesized from methyl esters with alcohols in good to excellent yield. Analysis of the catalyst solution revealed that basic species are generated by the ring-opening reaction of epoxide.

Amide/Iminium Zwitterionic Catalysts for (Trans)esterification: Application in Biodiesel Synthesis

A class of zwitterionic organocatalysts based on an amide anion/iminium cation charge pair has been developed. The zwitterions are easily prepared by reacting aziridines with aminopyridines. They are catalytically applicable to transesterifications and dehydrative esterifications. Mechanistic studies reveal that the amide anion and iminium cation work synergistically in activating the reaction partners, with the iminium cationic moiety interacting with the carbonyl substrates through nonclassical hydrogen bonding. The reaction can be applied to large-scale synthesis of biodiesel under mild conditions.

Chelation-Based Homologation by Reaction of Organometallic Reagents with O -Alkyl S -Pyridin-2-yl Thiocarbonates: Synthesis of Esters from Grignard Reagents

The one-carbon homologative esterification of Grignard reagents with O- alkyl S -pyridin-2-yl thiocarbonates has been explored. This one-step synthesis of esters from Grignard reagents is the first case to involve chelation-stabilized intermediates.

Sterically congested ester formation from α-substituted malononitrile and alcohol by an oxidative method using molecular oxygen

A metal-free oxidative esterification or thio-esterifica-tion of readily available substituted malononitrile and alcohol or thiol has been developed by simply mixing α-substituted malononitrile and alcohol or thiol in the presence of base under a molecular oxygen atmosphere. Sterically hindered ester or thioester can be prepared efficiently.

Aldehydes as potential acylating reagents for oxidative esterification by inorganic ligand-supported iron catalysis

The oxidative esterification of various aldehydes with alcohols could be achieved by a heterogeneous iron(iii) catalyst supported on a ring-like POM inorganic ligand under mild conditions, affording the corresponding esters, including several drug molecules and natural products, in high yields. ESI-MS and control experiments demonstrated that POM-FeV(O) was the active catalytic species and the plausible mechanism was presented. More importantly, the 6th run of the iron catalyst recycles shows only a slight decrease in the yield.

Alkoxycarbonylation of olefins with carbon dioxide by a reusable heterobimetallic ruthenium-cobalt catalytic system

The heterobimetallic ruthenium-cobalt catalytic system exhibited good catalytic performance and reusability in the reductive alkoxycarbonylation of olefins with carbon dioxide. Compared to the previous system only consisting of ruthenium catalyst, the binary catalyst system effectively reduced the usage of noble metal and ionic liquid additives. The respective contribution of ruthenium and cobalt catalysts in this multiple-step catalytic process was investigated by a series of condition-controlled experiments. The evolution of the ruthenium catalyst and the occurrence of alkene hydrogenation during the reaction was explained by theortical calculations.

Aerobic oxidative esterification and thioesterification of aldehydes using dibromoisocyanuric acid under mild conditions: No metal catalysts required

A practical direct method for the direct preparation of esters and thioesters from aldehydes is described. Esters and thioesters were synthesized by oxidative esterification and thioesterification via in situ generated acyl bromide intermediates, which were used to react with various alcohols and thiols. The esterification and thioesterification were readily performed in the presence of dibromoisocyanuric acid in dichloromethane, without any metal catalysts and under mild conditions. By using this reaction protocol, various esters and thioesters were prepared in high yields. This effective method offers a promising approach for the facile esterification and thioesterification of aldehydes.

Zn-Catalyzed tert-Butyl Nicotinate-Directed Amide Cleavage as a Biomimic of Metallo-Exopeptidase Activity

A two-step catalytic amide-to-ester transformation of primary amides under mild reaction conditions has been developed. A tert-butyl nicotinate (tBu nic) directing group is easily introduced onto primary amides via Pd-catalyzed amidation with tert-butyl 2-chloronicotinate. A weak base (Cs2CO3 or K2CO3) at 40-50 °C can be used provided that 1,1′-bis(dicyclohexylphosphino)ferrocene is selected as ligand. The tBu nic activated amides subsequently allow Zn(OAc)2-catalyzed nonsolvolytic alcoholysis in tBuOAc at 40-60 °C under neutral reaction conditions. The activation mechanism is biomimetic: the C3-ester substituent of the pyridine in the directing group populates the trans-conformer suitable for Zn-chelation, C=Oamide-Zn-Ndirecting group, and Zn-coordinated alcohol is additionally activated as a nucleophile by hydrogen bonding with the acetate ligand of the catalyst. Additionally, the acetate ligand assists in intramolecular O-to-N proton transfer. The chemoselectivity versus other functional groups and compatibility with challenging reaction partners, such as peptides, sugars, and sterols, illustrates the synthetic applicability of this two-step amide cleavage method. The tBu nic amides do not require purification before cleavage. Preliminary experiments also indicate that other weak nucleophiles can be used such as (hetero)arylamines (transamidation) as exemplified by 8-aminoquinoline.