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

HRID 1976288Notes

Reaction equation

HRID 1976288 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[C:10]1([CH3:17])[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[CH:11]=1.[C:18]1([CH:25]=[CH:24][CH:23]=[C:21]([OH:22])[CH:20]=1)[OH:19].[Cl-].[Cl-].[Cl-].[Al+3]>ClC1C=CC=CC=1>[OH:19][C:18]1[CH:20]=[C:21]([OH:22])[CH:23]=[CH:24][C:25]=1[C:2]1[N:4]=[C:5]([C:15]2[CH:14]=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[N:7]=[C:8]([C:15]2[CH:14]=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[N:1]=1

Participants

6

Reactant 4

HCID 5054ResorcinolHCID 7929M-XyleneHCID 7954Cyanuric chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 742762-(2,4-Dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
2 °C

Procedure

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.

Workup

  1. temperatureThe mixture was then warmed to 35° C.
  2. customquenched with ice and dilute aq. HCl
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. dissolutiondissolved in tetrahydrofuran
  6. additioncontaining 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
  7. additionThe only triazine product containing xylene

Sources & evidence

ORD record
ord-73eda564bdb14cedb87d7326ee4b760f
Source dataset
uspto-grants-2001_05
Patent number
US06225468B1

Reaction notes

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