5458-59-3Relevant articles and documents
Synthesis of Layered Disodium (or Dipotassium) Tetrakis-(octanoate-o)-Zinc(II) and Preliminary Investigation of the Catalytic Activity in the Esterification of Octanoic Acid with Isopropanol
Maruyama, Swami Arêa,Zawadzki, Sonia Faria,Wypych, Fernando
, p. 726 - 733 (2017)
This paper reports the synthesis of layered zinc/sodium and zinc/potassium octanoates (A2[Zn(C8H15O2)4], A = Na+ or K+), two underexplored carboxylates, through reaction of the octanoate of the desired alkali metal with a zinc salt. After drying and chemical characterization, their catalytic activities were tested in the esterification of octanoic acid with isopropanol. Conversion values were high for the reactions conducted under following conditions: temperature 155°C, isopropanol/octanoic acid molar ratio = 8: 1, catalyst/ octanoic acid ratio 7 wt %, and reaction time 2 h. Isolation of the catalysts after esterification showed that the materials were converted into zinc octanoate in situ.
1,3-Dibromo-5,5-dimethylhydantoin as a Precatalyst for Activation of Carbonyl Functionality
?ebular, Klara,Bo?i?, Bojan ?.,Stavber, Stojan
supporting information, (2019/08/01)
Activation of carbonyl moiety is one of the most rudimentary approaches in organic synthesis and is crucial for a plethora of industrial-scale condensation reactions. In esterification and aldol condensation, which represent two of the most important reactions, the susceptibility of the carbonyl group to nucleophile attack allows the construction of a variety of useful organic compounds. In this context, there is a constant need for development of and improvement in the methods for addition-elimination reactions via activation of carbonyl functionality. In this paper, an advanced methodology for the direct esterification of carboxylic acids and alcohols, and for aldol condensation of aldehydes using widely available, inexpensive, and metal-free 1,3-dibromo-5,5-dimethylhydantoin under neat reaction conditions is reported. The method is air- and moisture-tolerant, allowing simple synthetic and isolation procedures for both reactions presented in this paper. The reaction pathway for esterification is proposed and a scale-up of certain industrially important derivatives is performed.
Esterification of aryl/alkyl acids catalysed by n-bromosuccinimide under mild reaction conditions
?ebular, Klara,Bo?i?, Bojan ?.,Stavber, Stojan
, (2018/09/10)
N-halosuccinimides (NXSs) are well-known to be convenient, easily manipulable and low-priced halogenation reagents in organic synthesis. In the present work, N-bromosuccinimide (NBS) has been promoted as the most efficient and selective catalyst among the NXSs in the reaction of direct esterification of aryl and alkyl carboxylic acids. Comprehensive esterification of substituted benzoic acids, mono-, di- and tri-carboxy alkyl derivatives has been performed under neat reaction conditions. The method is metal-free, air- and moisture-tolerant, allowing for a simple synthetic and isolation procedure as well as the large-scale synthesis of aromatic and alkyl esters with yields up to 100%. Protocol for the recycling of the catalyst has been proposed.
