89611-20-1

Usage

InChI:InChI=1/C15H28O2/c1-2-3-4-5-6-10-13-17-15(16)14-11-8-7-9-12-14/h14H,2-13H2,1H3

Upstream product

• 111-87-5 octanol 
• 98-89-5 Cyclohexanecarboxylic acid 
• 108-93-0 cyclohexanol 
• 110-82-7 cyclohexane 
• 201230-82-2 carbon monoxide 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 54358-80-4 C₈H₁₄O₄S 
• 4630-82-4 methyl cyclohexylcarboxylate 
• 89611-19-8 Cyclohexanecarboxylic acid (Z)-2-dimethylcarbamoyl-1-methyl-vinyl ester 

Relevant academic research and scientific papers

Copper-Catalyzed Alkoxycarbonylation of Alkanes with Alcohols

Esters are important chemicals widely used in various areas, and alkoxycarbonylation represents one of the most powerful tools for their synthesis. In this communication, a new copper-catalyzed carbonylative procedure for the synthesis of aliphatic esters from cycloalkanes and alcohols was developed. Through direct activation of the C sp3 ?H bond of alkanes and with alcohols as the nucleophiles, the desired esters were prepared in moderate-to-good yields. Paraformaldehyde could also be applied for in situ alcohol generation by radical trapping, and moderate yields of the corresponding esters could be produced. Notably, this is the first report on copper-catalyzed alkoxycarbonylation of alkanes.

Efficient direct ester condensation between equimolar amounts of carboxylic acids and alcohols catalyzed by trifluoromethanesulfonic acid (TfOH) in Solkane365mfc

A simple, practical, and environmentally benign esterification protocol has been devised on the basis of TfOH as the catalyst and Solkane365mfc as the reaction medium. The direct condensation of equimolar amounts of various carboxylic acids and alcohols was conveniently carried out without recourse to any additional water removal technique, giving the desired carboxylic esters in excellent yields.

Esterification of free fatty acids (Biodiesel) using nano sulfated-titania as catalyst in solvent-free conditions

Nano sulfated titania was tested as catalyst for esterification of free fatty acids, specially methanolic and ethanolic esterification of stearic acid (biodiesels). Factorial design evidenced a positive effect of reaction temperature, amount of catalyst, and solvents on ester conversion. This nano-sized sulfated titania has been prepared by a sol-gel hydrothermal process. This prepared sulfated titania showed high catalytic activity in direct esterification of fatty acids as well as benzoic acids with various alcohols and phenols under solvent-free conditions. This method is of great value because of its environmentally benign character, easy handling, high yields, convenient operation, and green. FT-IR studies are shown that the catalyst can be reused for acylation without loss of catalytic activity.

Sulfonated polypyrene (S-PPR) as efficient catalyst for esterification of carboxylic acids with equimolar amounts of alcohols without removing water

Sulfonated polypyrene (S-PPR) efficiently catalyzed the reactions between carboxylic acids and equimolar amounts of alcohols with and without heptane to give the corresponding esters in good to excellent yields. Esterification was carried out at 110 °C without removing water. Transesterification of carboxylic esters with a slight excess of alcohols smoothly proceeded without heptane to give the corresponding esters in good yields. For these reactions, S-PPR was recycled without significant loss of activities.

Protic acid immobilized on solid support as an extremely efficient recyclable catalyst system for a direct and atom economical esterification of carboxylic acids with alcohols

(Chemical Equation Presented) A convenient and clean procedure of esterification is reported by direct condensation of equimolar amounts of carboxylic acids with alcohols catalyzed by an easy to prepare catalyst system of perchloric acid immobilized on silica gel (HClO4-SiO2). The direct condensation of aryl, heteroaryl, styryl, aryl alkyl, alkyl, cycloalkyl, and long-chain aliphatic carboxylic acids with primary/secondary alkyl/cycloalkyl, allyl, propargyl, and long-chain aliphatic alcohols has been achieved to afford the corresponding esters in excellent yields. Chiral alcohol and N-t-Boc protected chiral amino acid also resulted in ester formation with the representative carboxylic acid or alcohol without competitive N-t-Boc deprotection and detrimental effect on the optical purity of the product demonstrating the mildness and chemoselectivity of the procedure. The esters of long-chain (>C10) acids and alcohols are obtained in high yields. The catalyst is recovered and recycled without significant loss of activity. The industrial application of the esterification process is demonstrated by the synthesis of prodrugs of ibuprofen and a few commercial flavoring agents. Other protic acids such as H2SO4, HBr, TfOH, HBF4, and TFA that were adsorbed on silica gel were less effective compared to HClO4-SiO2 following the order HClO4-SiO 2 ? H2SO4-SiO2 > HBr-SiO 2 > TfOH-SiO2 ? HBF4-SiO2 ≈ TFA-SiO2. When HClO4 was immobilized on other solid supports the catalytic efficiency followed the order HClO4-SiO 2 > HClO4-K10 > HClO4-Al 2O3 (neutral) > HClO4-Al2O 3 (acidic) > HClO4-Al2O3 (basic).

Efficient condensation of carboxylic acids with alcohols catalyzed by fluorous ammonium triflates

The use of fluorous ammonium salts as metal-free catalysts for the direct condensation of equimolar amounts of carboxylic acids and aliphatic alcohols has been investigated. Esterification reactions were thus conveniently carried out under mild fluorous biphasic conditions, in the presence of 1 mol % of fluorous ammonium triflate and without recourse to any additional water removal technique. Good to excellent ester yields were obtained in the case of primary and secondary aliphatic alcohols. The fluorous salt was easily recovered by simple phase separation and reused at least three times without considerable loss of activity.

Mild, powerful, and robust methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively

We developed two efficient practical methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively. The present mild and robust reaction was performed by two separate methods both by combining cheap and readily available amines, N-methylimidazole, and N,N,N′,N′-tetramethylethylenediamine (TMEDA). Method A uses catalytic N-methylimidazole and TMEDA with an equimolar amount of K2CO3, whereas Method B uses equimolar amounts of N-methylimidazole and TMEDA. The salient features are as follows. (i) With regard to reactivity, Method B was superior to Method A for esterification and thioesterification, whereas cost-effective Method A was superior to Method B for amide formation. (ii) Amide formation proceeded smoothly between acid chlorides and less nucleophilic and stereocongested amines such as 2,6-dichloroaniline. (iii) This protocol was applied to the successful synthesis of two agrochemicals, bromobutide and carpropamid.

Bulky diarylammonium arenesulfonates as mild and extremely active dehydrative ester condensation catalysts

More environmentally benign alternatives to current chemical processes, especially large-scale, fundamental reactions like ester condensations, are highly desirable for many reactions. Bulky diarylammonium pentafluorobenzenesulfonates and tosylates serve as extremely active dehydration catalysts for the ester condensation reaction of carboxylic acids with equimolar amounts of sterically demanding alcohols and acid-sensitive alcohols. Typically, the esterification reaction is performed in heptane by heating at 80°C in the presence of 1 mol% of the catalyst without removing water. Esterification with primary alcohols proceeds without solvents even at room temperature. Furthermore, 4-(N-mesitylamino)polystyrene resin-bound pentafluorobenzenesulfonate can be recycled more than 10 times without a loss of activity.

METHOD FOR PRODUCING ESTER AND ESTERIFICATION CATALYST

A process for producing an ester includes the step of allowing a carboxylic acid to react with an alcohol, wherein an ammonium sulfonate is used as an esterification catalyst, the ammonium sulfonate being composed of an ammonium cation having a basic skeleton represented by formula (1) (wherein n represents 1 or 2) in which hydrogen atoms in the benzene rings and hydrogen atoms bonded to bridge carbon may be substituted), and a sulfonic acid anion represented by RSO 3 - (wherein R represents an arene, a perfluoroalkane having 1 to 8 carbon atoms, or a bulky alkane).