Synthesis of Adamantylated Salicylic Acids

5-[3(4)-R-Adamantan-1-yl]salicylic acids [R = H, Alk, Ar, OH, NHC(S)NH2] have been synthesized by electrophilic substitution reactions of hydroxy- and bromoadamantanes with salicylic acid, as well as by reactions of 5-(3-hydroxyadamantan-1-yl)salicylic acid with carbon and nitrogen nucleophiles, in trifluoroacetic acid. The possibility of selective hydroxylation of the adamantane fragment in 5-(adamantan-1-yl)salicylic acid with sulfuric acid in trifluoroacetic anhydride has been demonstrated.