The Friedel-Crafts Reaction of Chloro-s-triazines with Aromatic Compounds and the Synthesis of their Derivatives. III.

Abstract

The Friedel-Crafts reaction of anisole with each one of cyanuric chloride, 2, 4-dichloro-6-methoxy-s-triazine (DCMT), and 2-chloro-4, 6-dimethoxy-s-triazine (CDMT), and the demethylation of their products were investigated. When cyanuric chloride was treated with an equivalent amount of anisole in carbon disulfide, 2, 4, 6-tris(p-methoxyphenyl)-s-triazine (TPMT) (19.4% yield), a condensation product, and hydroxy-phenyltriazine and phenoxytriazine, products from demethylated anisole, were obtaind. In the presence of excess anisole, TPMT (44.3/ yield) and 2-p-methoxyphenyl-4, 6-his (o-methoxyphenyl)-s-triazine (30. 4/ yield) were obtained as condensation products, and no demethylation product was found. In the reaction with DCMT, 2, 4-his (p-methoxyphenyl)-s-triazine-6 (1H)-one was obtained. In the reaction with CDMT, however, only demethylation and rearrangement of CDMT were noted without the formation of condensation product. Demethylation of TPMT was conducted in the presence of anhydrous aluminum chloride in benzene to yield 2, 4, 6-tris (p-hydroxyphenyl)-s-triazine (63% yield).