102245-28-3Relevant academic research and scientific papers
Water solvent method for esterification and amide formation between acid chlorides and alcohols promoted by combined catalytic amines: Synergy between N-methylimidazole and N,N,N′,N′-tetramethylethylenediamine (TMEDA)
Nakatsuji, Hidefumi,Morita, Jun-Ichi,Misaki, Tomonori,Tanabe, Yoo
, p. 2057 - 2062 (2006)
An efficient method for esterification between acid chlorides and alcohols in water as solvent has been developed by combining the catalytic amines, N-methylimidazole and N,N,N′,N′-tetramethylethylenediamine (TMEDA). The present Schotten-Baumann-type reaction was performed by maintaining the pH at around 11.5 using a pH controller to prevent the decomposition of acid chlorides and/or esters and to facilitate the condensation. The choice of catalysts (0.1 equiv.) was crucial: the combined use of N-methylimidazole and TMEDA exhibited a dramatic synergistic effect. The catalytic amines have two different roles: (i) N-methylimidazole forms highly reactive ammonium intermediates with acid chlorides and (ii) TMEDA acts as an effective HCl binder. The production of these intermediates was rationally supported by a careful 1H NMR monitoring study. Related amide formation was also achieved between acid chlorides and primary or secondary amines, including less nucleophilic or water-soluble amines such as 2-(or 4-)chloroaniline, the Weinreb N-methoxyamine, and 2,2-dimethoxyethanamine.
Co-oxidation of octane and benzaldehyde using molecular oxygen with Au-Pd/carbon prepared by sol-immobilisation
Peneau, Virginie,Shaw, Greg,Freakley, Simon J.,Forde, Michael M.,Dimitratos, Nikolaos,Jenkins, Robert L.,Taylor, Stuart H.,Hutchings, Graham J.
, p. 3953 - 3959 (2015/08/03)
The selective oxidation of linear alkanes with molecular oxygen under mild conditions remains a challenging topic in the field of catalysis. In this study we investigate the co-oxidation of C-H bonds in substrates with different relative reactivities, the aim being to couple the oxidised products in situ to form the corresponding esters. Initial attempts were made to co-oxidise octane with toluene to form octyl benzoate using Au-Pd catalysts. During the study the oxidation of octane in the presence of benzaldehyde, an oxidation product of toluene, was also investigated in order to demonstrate the potential feasibility of the reaction. This work summarises our attempts to show whether a co-oxidation system could be an effective way to oxidise linear alkanes.
Mild, powerful, and robust methods for esterification, amide formation, and thioesterification between acid chlorides and alcohols, amines, thiols, respectively
Nakatsuji, Hidefumi,Morimoto, Mami,Misaki, Tomonori,Tanabe, Yoo
, p. 12071 - 12080 (2008/03/13)
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.
Solvolysis of N-n-Alkylacridiniums in Phenol and Carboxylic Acids. Primary Carbonium Ions as Possible Intermediates
Katritzky, Alan R.,El-Mowafy, Azzahra M.
, p. 3511 - 3517 (2007/10/02)
N-n-Octyl (1a) and N-n-dodecylacridinium (1b) ions solvolyze in phenol to give mixtures of the n-alkyl phenyl ethers and all the isomeric secondary straight-chain o- and p-alkylphenols.Solvolyses of 1a in carboxylic acids give a mixture of 1-, 2-, 3-, and 4-octyl carboxylic esters.Structures are deduced by GC/MS.Mechanisms are discussed.
