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A by-product provided by the producer of 2-methyl-3-furanthiol was characterized by 1D and 2D NMR, GC–MS (EI) and HRMS analyses. It was identified to be 4-(5-methyl-2-furylthio)-5-methyltetrahydrofuran-2-thione and its precursor 2-methyl-5-thioacetylfuran… Click to show full abstract
A by-product provided by the producer of 2-methyl-3-furanthiol was characterized by 1D and 2D NMR, GC–MS (EI) and HRMS analyses. It was identified to be 4-(5-methyl-2-furylthio)-5-methyltetrahydrofuran-2-thione and its precursor 2-methyl-5-thioacetylfuran was also determined. 2-Methyl-5-thioacetylfuran was formed by the nucleophilic addition of AcSH to the aldehyde group of 4-oxo-2-pentenal during the industrial production of 2-methyl-3-furanthiol. The hydrolysis of 2-methyl-5-thioacetylfuran under basic conditions gave 5-methyl-2-furanthiol, which underwent autothiylation to lead to the formation of 4-(5-methyl-2-furylthio)-5-methyltetrahydrofuran-2-thione.
Journal Title: Flavour and Fragrance Journal
Year Published: 2017
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