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

HRID 987999Notes

Reaction equation

HRID 987999 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[Cl-].[Al+3].[Cl-].[Cl-].Cl.[C:15]1([CH:22]=[CH:21][CH:20]=[C:18]([OH:19])[CH:17]=1)[OH:16].[CH3:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=1[CH3:30]>C1C=CC(Cl)=C(Cl)C=1.O>[OH:16][C:15]1[CH:17]=[C:18]([OH:19])[CH:20]=[CH:21][C:22]=1[C:2]1[N:4]=[C:5]([C:26]2[CH:27]=[CH:28][C:29]([CH3:30])=[C:24]([CH3:23])[CH:25]=2)[N:7]=[C:8]([C:26]2[CH:27]=[CH:28][C:29]([CH3:30])=[C:24]([CH3:23])[CH:25]=2)[N:1]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5054ResorcinolHCID 7237O-XyleneHCID 7954Cyanuric chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1358045052-(2,4-Dihydroxyphenyl)-4,6-bis(3,4-dimethylphenyl)-1,3,5-triazineYield 93.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 72391,2-DichlorobenzeneSolvent2×

Conditions

Temperature
5 °C

Procedure

To a flask equipped with a reflux condenser, a nitrogen inlet, and a mechanical stirrer is added 50 gm of cyanuric chloride, 191 mL of ODCB and 108.4 gm of aluminum chloride. The mixture is cooled in an ice-bath to 5° C. and 6.5 gm of concentrated HCl was added over a period of 20 minutes. The mixture was allowed to warm to room temperature, and stirred for 2 hours. It was cooled back to 5° C. and then 54.7 gm of o-xylene was slowly added over a period of 3 hours, while allowing the temperature to go up to 21° C. The mixture was stirred at room temperature for additional 16 hours. The reaction mixture was heated to about 63° C. and 34 gm of resorcinol was added over a period of about 30 minutes. The mixture was held at about 75° C. for 3 hours. It was then added to 500 mL water and ODCB distilled off azeotropically. The precipitated solid was filtered off and washed with water. The material was dried in a vacuum oven to give 96 gm of crude 2-(2,4-dihydroxyphenyl)-4,6-bis(3,4-dimethylphenyl)-1,3,5-triazine. The HPLC analysis showed it to contain about 5% of polyresorcinol-triazines and 10.7% tris-o-xylyl-triazine.

Workup

  1. customTo a flask equipped with a reflux condenser, a nitrogen inlet, and a mechanical stirrer
  2. temperatureto warm to room temperature
  3. temperatureIt was cooled back to 5° C.
  4. customto go up to 21° C
  5. stirringThe mixture was stirred at room temperature for additional 16 hours
  6. temperatureThe reaction mixture was heated to about 63° C.
  7. waitThe mixture was held at about 75° C. for 3 hours
  8. distillationdistilled off azeotropically
  9. filtrationThe precipitated solid was filtered off
  10. washwashed with water
  11. customThe material was dried in a vacuum oven

Sources & evidence

ORD record
ord-798596a466474f088bc1d5a876fe0ebb
Source dataset
uspto-grants-2003_10
Patent number
US06632944B2

Reaction notes

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