Process for making 2-(2,4-dihydroxyphenyl) or 2-(2,4-dialkoxyphenyl)-4,6-Bisaryl-1,3,5-triazines
A triazine compound, C1-C24 technology, applied in organic chemistry methods, chemical instruments and methods, organic chemistry and other directions, can solve problems such as expensive raw materials
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Embodiment 1
[0159] Example 1: 2-(2,4-Dihydroxyphenyl)-4,6-bis-(2,4-dimethylphenyl)s-triazine (4). With 2.5 equivalents of aluminum trichloride.
[0160] 3.35 g of aluminum chloride (2.5 equivalents, based on cyanuric chloride) were added to a stirred mixture of 1.84 g of cyanuric chloride, 1.1 gm of resorcinol, 2.5 ml of m-xylene and 25 ml of chlorobenzene at 5°C. The reaction mixture was stirred at 5°C for 2 hours, then at 15°C for 4 hours and finally at room temperature for 24 hours. The reaction mixture was analyzed by TLC and HPLC. HPLC analysis demonstrated the formation of only two major products, 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. And the formed two resorcinol-based product 2,4-bis(2,4-dihydroxyphenyl)-6-(2,4-dimethylphenyl)-1,3,5-triazine (3 ) is only a minor component, the ratio of 4:3 is 97:3. 2-Chloro-4,6-bis(2,4-dihydroxyphenyl) s-triazine (2) is only 0.36%, 2,4 , 6-tris-(2,4-dihydroxyphen...
Embodiment 2
[0161] Example 2: 2-(2,4-Dihydroxyphenyl)-4,6-bis-(2,4-dimethylphenyl)-s-triazine (4). Use 2.25 equivalents of aluminum trichloride.
[0162]Under a nitrogen atmosphere, a mixture of 10 g cyanuric chloride (0.0542 mol), 11.51 g m-xylene (2 eq) and 5.97 g resorcinol (1 eq) in 100 ml chlorobenzene was cooled to 2°C. Aluminum trichloride (16.26 g, 2.25 equiv) was added over 25 minutes maintaining the temperature below 5°C. It was then stirred and heated to 25°C and the progress of the reaction was monitored by HPLC (area % at 290 nm). After 24 hours at 25°C, HPLC analysis showed 37.6% of 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-s-triazine (4) while only 1.0%1, 4.4%2 and 5.1%3. Additional m-xylene (2 equiv) and aluminum trichloride (0.25 equiv) were added and the mixture was heated to 32-35°C for 20 hours. HPLC analysis showed that the yield of 1 increased to 45.3%, and only 1.9% 2,4,6-tri-(2,4-dihydroxyphenyl)-5-triazine and 5.6% 2,4-bis-(2 , 4-dihydroxyphenyl)-6-...
Embodiment 3
[0163] Example 3: 2-(2,4-Dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-s-triazine (4). 2.25 equivalents of aluminum trichloride are used; the initial reaction temperature is 35°C.
[0164] Under a nitrogen atmosphere, a mixture of 10 g cyanuric chloride (0.0542 mol), 11.51 g m-xylene (2 eq) and 5.97 g resorcinol (1 eq) in 100 ml chlorobenzene was cooled to 2°C. Aluminum trichloride (16.26 g, 2.25 equiv) was added over 25 minutes maintaining the temperature below 5°C. It was then stirred and heated to 35°C and the progress of the reaction was monitored by HPLC (area % at 290 nm). After 23 hours at 35°C, HPLC analysis showed 47.4% of 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-s-triazine (4) While only 7.6% of 2,4-bis-(2,4-dihydroxyphenyl)-6-(2,4-dimethyl)-s-triazine (3), no unreacted cyanuric chloride. Additional m-xylene (28.77 g) and 5.43 g of aluminum trichloride (0.75 equiv) were added and the mixture was heated to 55-60° C. for 24 hours. HPLC analysis indicated ...
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