Synthesis of S-Methyl 2-Hydrxyalkanethioates, 2-Hydroxyalkanoic Acids and Related Compounds via the Addition Reaction of Tris(methylthio)methanide Ion to Alkanals

Article abstract of DOI:10.1246/bcsj.62.2013

In connection with the studies on biological activities on myrmicacin and related compounds, the synthetic method for 2-hydroxyalkanoic acids and the corresponding 1,2-diols was studied.The addition reaction of tris(methylthio)methyllithium to the aldehydes (propanal-dodecanal) gave the corresponding 1,1,-tris(methylthio)-2-alkanols 1a-j.Treatment of 1 with mercury(II) chloride-mercury(II) oxide in water-acetone afforded S-methyl 2-hydroxyalkanethioates 2a-j, and in methanol methyl 2-hydroxyalkanoates 3c-j were obtained.Reduction of the thioates 2 with lithium aluminium hydride gave 1,2-diols 4c-j and saponification produced the corresponding 2-hydroxyalkanoic acids 5c-j.