LAUSR

Synthesis of seleniumand tellurium-containing analogues of natural and synthetic antioxidants is one of directions of creation of highly eff ective oxidation inhibitors used nowadays.1—3 In our opinion, (alkylsulfanyl)methylsubstituted phenols are potential prototypes for development of their selenium-containing analogues. However, existing methods of synthesis of (alkylselanyl)methylphenols consist of multiple stages: they include protection of phenolic OH group, bromomethylation, substitution of halogen by selenium-containing group, and fi nal de protection; this defi nes their labor intensity and low yield. Thus, total yields of biphenyl-4,4 ́-diol-based4 and 3-(4-hydroxyphenyl)propionic acid-based5 derivatives are 8% and 24%, respectively. The yield of conversion of 3,5-bis(hydroxymethyl)phenol to 3,5-bis[(phenylselanyl) methyl] phenol6 without protection of phenolic ОН group is 41%. It is known that (alkylsulfanyl)methylphenols can be synthesized in one stage in high yields by condensation of phenols, thiols, and formaldehyde.7,8 Equivalent conversion with selenols is not reported; thus, it is appropriate to investigate possibility to carry out this synthesis and evaluate its potential to produce (alkylselanyl)methylphenols. We found that within the fi rst hour of reaction of 2,6-dimethylphenol with formaldehyde and dodecaneselenol (obtained in situ by reduction of bis(dodecyl) diselenide with NaBH4) in the presence of KOH, virtually full conversion of the initial phenol and formation of the intermediate 4-hydroxymethyl-2,6-dimethylphenol takes place. The intermediate converts to 4-[(dodecylselanyl)methyl]-2,6-dimethylphenol (1) within next two hours (Scheme 1). According to GC/MS analysis, the reaction mixture consists of 91.6% of 1, 3.6% of 4-ethoxymethyl-