M-Cresol → 2-(2-Hydroxy-4-methylphenyl)-4,6-bis(4-phenoxyphenyl)-1,3,5-triazine

HRID 23852

Reaction equation

HRID 23852 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][CH:9]=2)[N:5]=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:23][CH:22]=2)[N:3]=1.[CH:34]1[C:39]([OH:40])=[CH:38][CH:37]=[CH:36][C:35]=1[CH3:41].[Al+3].[Cl-].[Cl-].[Cl-].N1C=CC=NN=1>ClC1C=CC=CC=1>[OH:40][C:39]1[CH:34]=[C:35]([CH3:41])[CH:36]=[CH:37][C:38]=1[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][CH:9]=2)[N:5]=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:23][CH:22]=2)[N:3]=1

Participants

6

Reactant 4

HCID 342M-CresolHCID 1230471,2,3-TriazineHCID 6451240Aluminum(III) ChlorideHCID 225686182-Chloro-4,6-bis(4-phenoxyphenyl)-1,3,5-triazine

Product 1

HCID 1356219502-(2-Hydroxy-4-methylphenyl)-4,6-bis(4-phenoxyphenyl)-1,3,5-triazine

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 0.9 gm of 2-chloro-4,6-bis(4-phenoxyphenyl)-1,3,5-triazine, 0.24 gm of m-cresol and 0.4 gm AlCl3 in 5 ml chlorobenzene was heated to 70° C. under nitrogen and efficient stirring. After about 4 hr at 70° C., the reaction mixture was analyzed by HPLC, which showed the formation of a new product, and almost disappearance of the starting triazine. The reaction mixture was cooled to room temperature and quenched with water. It was then extracted with methylene chloride, and the organic layer separated, washed with water, dried, and concentrated to give a crude product. The crude product was crystallized from acetone to give pure 2-(2-hydroxy-4-methylphenyl)-4,6-bis(4-phenoxyphenyl)-1,3,5-triazine identified by HPLC, NMR and mass spectroscopy.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with water
  3. extractionIt was then extracted with methylene chloride
  4. customthe organic layer separated
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. customto give a crude product
  9. customThe crude product was crystallized from acetone

Sources & evidence

ORD record
ord-baa520823cef4fca827501002f305f40
Source dataset
uspto-grants-2005_02
Patent number
US06855269B2

Linked notes

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