S-(HYDROXYMETHYL) 4-HYDROXYPHENYL SULFIDES: SYNTHESIS AND SELECTED CHEMISTRY OF SOME STABLE HEMIMERCAPTALS

Abstract

The base-catalyzed reaction of 3,5-di-tert-butyl-4-hydroxybenzenethiol (1a), 3-tert-butyl-4-hydroxy-5-methylbenzenethiol (1b), and 4-hydroxybenzenethiol (1c) with formaldehyde gave the corresponding hemimercaptal derivatives 2a–c, respectively. The stable hemimercaptals 2a–c were characterized by IR, ¹H NMR, ¹³C NMR, MS and elemental analysis. The ester of 2a with 3-(3,5-di-tert-butyl-4-hydroxy-phenyl)propanoic acid (3a) was prepared using triphenylphosphine and diethyl azodicarboxylate (Mitsunobu conditions).