Premium
Identification of an unusual by‐product in the industrial production of 2‐Methyl‐3‐furanthiol
Author(s) -
Ding Rui,
Zhang Shishi,
He Dawei,
Liu Yongguo,
Yang Shaoxiang,
Sun Baoguo,
Tian Hongyu
Publication year - 2017
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.3409
Subject(s) - chemistry , aldehyde , hydrolysis , methyl group , nucleophile , organic chemistry , stereochemistry , group (periodic table) , catalysis
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.