Resorcinol → 2-(2,4-Dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.84 g cyanuric chloride (10 mmol), 2.12 g of m-xylene (2 eq.), and 1.10 g of resorcinol (1 eq.) in 20 mL chlorobenzene under a nitrogen atmosphere was cooled to 2° C. Aluminum trichloride (2.12 g, 1 eq.) was added over 2 mm. The mixture was then warmed to 35° C. with stirring. After 22 hr., a sample was taken and quenched with ice and dilute aq. HCl. The resulting precipitate was filtered, washed with water, dissolved in tetrahydrofuran and analyzed by HPLC. HPLC analysis (area % at 290 nm) showed mainly tris- and bis-resorcinol containing triazine products 2,4,6-tris-(2,4-dihydroxyphenyl)-s-triazine (1) and 2-chloro-4,6-bis-(2,4-dihydroxyphenyl)-s-triazine (2) with no m-xylyl substitution. The ratio of 1 to 2 was 21:78. Unreacted m-xylene was also present. The only triazine product containing xylene observed was bisresorcinol-triazine based 2,4-bis-(2,4-dihydroxyphenyl)-6-(2,4-dimethylphenyl)-s-triazine 3. The monoresorcinol-triazine based product, 2-(2,4-dihydroxyphenyl)-4,6-bis-(2,4-dimethylphenyl)-s-triazine 4 was not formed.

Provenance & Evidence