Resorcinol → 2,4-Bis(2,4-dihydroxyphenyl)-6-(2,4-dimethylphenyl)-s-triazine

Participants

Reaction Conditions

Reaction Steps

To a stirring mixture of 1.84 g of cyanuric chloride, 1.1 gm of resorcinol, 2.5 mL of m-xylene and 25 mL of chlorobenzene was added 3.35 g of aluminum chloride (2.5 eq. based on cyanuric chloride) at 5° C. The reaction mixture was stirred at 5° C. for 2 h, then at 15° C. for 4 hr and finally at room temperature for 24 hr. The reaction mixture was analyzed by TLC and HPLC. The HPLC analysis confirmed the formation of 2-(2,4-dihydroxyphenyl)-4,6-(2,4-dimethylphenyl)-1,3,5-triazine (4) and 2,4,6-tris(2,4-dimethylphenyl)-1,3,5-triazine as the only two major products. The bisresorcinol based product, 2,4-bis(2,4-dihydroxyphenyl)-6-(2,4-dimethylphenyl)-1,3,5-triazine (3), was formed only as a minor component and the ratio of 4:3 was 97:3. The 2-chloro-4,6-bis(2,4-dihydroxyphenyl)s-triazine (2) was only 0.36% and 2,4,6-tris-(2,4-dihydroxyphenyl)-s-triazine (1) was 0.5%. The experiment demonstrated the preferential formation of monoresorcinol based product 4 by reacting cyanuric chloride, resorcinol, m-xylene and aluminum chloride simultaneously with higher charge of aluminum chloride.

Provenance & Evidence