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

HRID 1066439Notes

Reaction equation

HRID 1066439 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[CH3:22])[N:12]=[C:11](OC2C=CC=CC=2)[N:10]=1.[C:30]1([CH:37]=[CH:36][CH:35]=[C:33]([OH:34])[CH:32]=1)[OH:31].[Cl-].[Al+3].[Cl-].[Cl-].C1S(=O)(=O)CCC1.Cl>>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[CH3:22])[N:12]=[C:11]([C:35]2[CH:36]=[CH:37][C:30]([OH:31])=[CH:32][C:33]=2[OH:34])[N:10]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 5054ResorcinolHCID 31347SulfolaneHCID 6451240Aluminum(III) ChlorideHCID 108942254,6-Bis-(2,4-dimethylphenyl)-2-phenoxy-s-triazine

Product 1

HCID 742762-(2,4-Dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazineYield 69%

Conditions

Temperature
160 °C

Procedure

To a 250 mL round-bottomed flask equipped with a magnetic stirrer, a condenser and a nitrogen atmosphere are added 6.00 g (0.0157 mol) of the product of Example 2, 2.08 g (0.0189 mol) of resorcinol, 2.09 g (0.0157 mol) of aluminum chloride and 6 mL of tetramethylene sulfone (sulfolane). The mixture is stirred at 138° C. for six hours, 147° C. for seven hours, 160° C. for 10.5 hours and then allowed to cool to room temperature. A portion of 2N hydrochloric acid is added and the mixture is refluxed for two hours and then allowed to cool to room temperature. The solids formed are collected by vacuum filtration and then washed with portions of water and heptane. The crude solid is taken up in ethyl acetate and passed through a plug of silica gel. The solvent is removed under reduced pressure to give 5.25 g of crude product. The crude product is recrystallized from methanol to afford 4.29 g (69% yield) of the title compound as a yellow solid melting at 199-201° C.

Workup

  1. customTo a 250 mL round-bottomed flask equipped with a magnetic stirrer, a condenser
  2. temperatureto cool to room temperature
  3. temperaturethe mixture is refluxed for two hours
  4. temperatureto cool to room temperature
  5. customThe solids formed
  6. filtrationare collected by vacuum filtration
  7. washwashed with portions of water and heptane
  8. customThe solvent is removed under reduced pressure
  9. customto give 5.25 g of crude product
  10. customThe crude product is recrystallized from methanol

Sources & evidence

ORD record
ord-617de7914ce445958e0ee203d0df9955
Source dataset
uspto-grants-2001_06
Patent number
US06242598B1

Reaction notes

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