Synthesis of 2,15-hexadecanedione as a precursor of Muscone

Abstract

Muscone is a precious fragrant compound, which is scarce in nature, many synthetic attempts for this unique natural product have been carried out. A new synthetic method for 2,15-hexadecanedione, a precursor of muscone, from imidazalium salt and di-Grignard reagent is reported. Imidazalium salt was used as tetrahydrofolate coenzyme model at formic acid oxidation level and di-Grignard reagent as nucleophile to which one-carbon unit was transferred, the biomimetic synthesis of 2,15-hexadecanedione was successfully accomplished by using the addition-hydrolysis reaction of imidazolium salt with di-Grignard reagent. A novel method for preparing muscone is provided.

A theoretical study on the mechanism of a novel one-carbon unit transfer reaction

“…Using imidazoline or benzimidazolium compounds as tetrahydrofolate coenzyme models, Shi et al have successfully synthesized aldehydes, ketones, large-ring cycloalkanones, and other organic compounds [7][8][9][10][11][12][13]. In the process of these biomimetic reactions, the one-carbon unit transfers from the THF models to the nucleophilic reagents at the formic acid oxidation level.…”

An Efficient and Green Synthesis of Benzimidazole Derivatives Using SBA-15 Supported Cobalt Nanocatalysts

“…Apart from therapeutic applications, benzimidazoles also play an important role as intermediates in different organic reactions [7,8]. Two general methods are reported for the synthesis of 2-substituted benzimidazoles;…”

Synthesis of 2-substituted benzimidazoles and benzothiazoles using Ag2CO3/Celite as an efficient solid catalyst

“…This effect can be explained by a simple acid-catalysis mechanism facilitated by the strong hydrogen bond interaction at the organic-water or ethanol interface which stabilizes the reaction intermediate. Next, we studied the model reaction in ethanol at different temperatures (Table 1, entry 1 and entries [10][11][12]. The reaction rate increased as the temperature was raised.…”