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

HRID 1976289Notes

Reaction equation

HRID 1976289 reaction equation
N1C(Cl)=NC(Cl)=NC=1Cl.[C:10]1([CH:17]=[CH:16][CH:15]=[C:13]([OH:14])[CH:12]=1)[OH:11].[Cl-].[Al+3].[Cl-].[Cl-].[OH:22][C:23]1[CH:28]=[C:27]([OH:29])[CH:26]=[CH:25][C:24]=1[C:30]1[N:35]=[C:34](C2C=CC(C)=CC=2C)[N:33]=[C:32]([C:44]2[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][C:45]=2[CH3:51])[N:31]=1.CC1C=C(C)C=CC=1C1N=C(C2C=CC(C)=CC=2C)N=C(C2C=CC(C)=CC=2C)N=1>ClC1C=CC=CC=1.C1(C)C=CC=C(C)C=1>[OH:11][C:10]1[CH:12]=[C:13]([OH:14])[CH:15]=[CH:16][C:17]=1[C:34]1[N:35]=[C:30]([C:24]2[CH:25]=[CH:26][C:27]([OH:29])=[CH:28][C:23]=2[OH:22])[N:31]=[C:32]([C:44]2[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][C:45]=2[CH3:51])[N:33]=1

Participants

8

Reactant 5

HCID 5054ResorcinolHCID 7954Cyanuric chlorideHCID 742762-(2,4-Dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazineHCID 6451240Aluminum(III) ChlorideHCID 224759882,4,6-Tris(2,4-dimethylphenyl)-1,3,5-triazine

Product 1

HCID 1355454222,4-Bis(2,4-dihydroxyphenyl)-6-(2,4-dimethylphenyl)-s-triazine

Reagents, catalysts & solvents 2

HCID 7929M-XyleneSolventHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
5 °C

Procedure

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.

Workup

  1. waitat 15° C. for 4 hr
  2. waitfinally at room temperature for 24 hr

Sources & evidence

ORD record
ord-3e111c605e86406d9f4b24c944f7c2b1
Source dataset
uspto-grants-2001_05
Patent number
US06225468B1

Reaction notes

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