Hydrochloric Acid → 2,4-Bis(2,4-dihydroxy-5-hexylphenyl)-6-phenyl-s-triazine

HRID 265829

Reaction equation

HRID 265829 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:19]([C:25]1[CH:31]=[CH:30][C:28]([OH:29])=[CH:27][C:26]=1[OH:32])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].Cl>S1(CCCC1)(=O)=O.CO.O>[OH:29][C:28]1[CH:27]=[C:26]([OH:32])[C:25]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:31][C:30]=1[C:2]1[N:7]=[C:6]([C:30]2[CH:31]=[C:25]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:26]([OH:32])=[CH:27][C:28]=2[OH:29])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 3610HexylresorcinolHCID 155492,4-Dichloro-6-phenyl-1,3,5-triazineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1358435902,4-Bis(2,4-dihydroxy-5-hexylphenyl)-6-phenyl-s-triazine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 31347SulfolaneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a 750 mL sulfonation flask equipped with a mechanical stirrer, condenser, dropping funnel and a nitrogen atmosphere are charged 34.0 g (150 mmol) of 2,4-dichloro-6-phenyl-s-triazine, 44.0 g (330 mmol) of aluminum chloride and 100 mL of ligroin (boiling range 110°-140° C.). To that suspension, 60 mL of sulfolane are added dropwise with stirring over a 15 minute period with the temperature rising to 50° C. A solution of 62.1 g (320 mmol) of 4-hexylresorcinol in 60 mL of sulfolane is then added dropwise over a 15 minute period. The temperature rises to 60° C. and hydrogen chloride is evolved. The reaction mixture is heated to 80° C. for four hours. The lower layer of the two-phase mixture is poured into a solution of 50 mL of concentrated hydrochloric acid in 500 mL of methanol and 300 mL of water. The mixture is stirred at room temperature for 14 hours. The product obtained is suspended in 800 mL of water at 80° C. for 1 hour, is isolated by filtration and resuspended under the same conditions, finally isolated and dried at 85° C. under vacuum. The title compound is obtained as a crude orange product (77.0 g) and melts at 230°-238° C. It can be used without further purification.

Workup

  1. customTo a 750 mL sulfonation flask equipped with a mechanical stirrer, condenser
  2. customrising to 50° C
  3. customrises to 60° C.
  4. stirringThe mixture is stirred at room temperature for 14 hours
  5. customThe product obtained
  6. customis isolated by filtration
  7. customfinally isolated
  8. customdried at 85° C. under vacuum

Sources & evidence

ORD record
ord-3fab83c60bb24d3dbc634d98109c47e6
Source dataset
uspto-grants-1997_07
Patent number
US05648488

Linked notes

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