Resorcinol → 2,4-Bis(2,4-dihydroxyphenyl)-6-(4-phenoxyphenyl)-1,3,5-triazine

HRID 23853

Reaction equation

HRID 23853 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[Cl-].[Al+3].[Cl-].[Cl-].[C:14]1([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:27]1([CH:34]=[CH:33][CH:32]=[C:30]([OH:31])[CH:29]=1)[OH:28]>ClC1C=CC=CC=1Cl>[OH:28][C:27]1[CH:29]=[C:30]([OH:31])[CH:32]=[CH:33][C:34]=1[C:2]1[N:4]=[C:5]([C:32]2[CH:33]=[CH:34][C:27]([OH:28])=[CH:29][C:30]=2[OH:31])[N:7]=[C:8]([C:24]2[CH:23]=[CH:22][C:21]([O:20][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:26][CH:25]=2)[N:1]=1

Participants

6

Reactant 4

HCID 5054ResorcinolHCID 7583Diphenyl EtherHCID 7954Cyanuric chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1356219532,4-Bis(2,4-dihydroxyphenyl)-6-(4-phenoxyphenyl)-1,3,5-triazineYield 10.1%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

To a stirring mixture of 9 gm of cyanuric chloride, 20 gm of aluminum chloride in 50 mL of o-dichlorobenzene was added 8.5 gm of phenyl ether followed by 11 gm of resorcinol. The reaction mixture was first stirred at room temperature and then gradually heated to 110-115° C., and then held for 4 hr at this temperature. The heating was discontinued, and the reaction mixture quenched with water. O-Dichlorobenzene was removed azeotropically from the product mixture, the precipitated material filtered, and washed with water. The crude product was purified by column chromatography to give 2.3 gm of pure 2,4-bis(2,4-dihyroxyphenyl)-6-(4-phenoxyphenyl)-1,3,5-triazine, identified by HPLC, NMR, LC-UV and mass spectroscopy.

Workup

  1. temperaturegradually heated to 110-115° C.
  2. customthe reaction mixture quenched with water
  3. customO-Dichlorobenzene was removed azeotropically from the product mixture
  4. filtrationthe precipitated material filtered
  5. washwashed with water
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-96e90055b36f4eb2b8f7413ef1d79199
Source dataset
uspto-grants-2005_02
Patent number
US06855269B2

Linked notes

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