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Alpha-Methylstyrene → 2-[2,4-Dihydroxy-5-(1-methyl-1-phenylethyl)phenyl]-4,6-bis-phenyl-s-triazin

HRID 1488838
Notes
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Reaction equation

HRID 1488838 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:12]=[C:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:10]=1.CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].[CH3:40][C:41]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[CH2:42]>CCCCCCC>[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([C:41]([CH3:42])([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH3:40])=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:14]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7407Alpha-MethylstyreneHCID 11143Aluminum isopropoxideHCID 1354371252-(2,4-Dihydroxyphenyl)-4,6-diphenyl-1,3,5-triazine

Product 1

HCID 1358436022-[2,4-Dihydroxy-5-(1-methyl-1-phenylethyl)phenyl]-4,6-bis-phenyl-s-triazinYield 65.9%

Reagents, catalysts & solvents 1

HCID 8900Heptane
Solvent

Conditions

Temperature
160 °C

Procedure

To a 500 mL three-necked, round-bottomed flask equipped with a magnetic stirrer, dropping funnel, condenser, thermometer, and a nitrogen atmosphere are charged 5.00 g (14.7 mmol) of 2-(2,4-dihydroxyphenyl)4,6-bis-phenyl-s-triazine and 300 mg of aluminum isopropoxide. The mixture is heated to 160° C. and 17.3 g of a-methylstyrene are added all at once. After stirring at this temperature for 26 hours the mixture is allowed to cool and a potion of heptane is added. Vacuum filtration affords 4.45 g of the title compound as a yellow solid.

Workup

  1. customTo a 500 mL three-necked, round-bottomed flask equipped with a magnetic stirrer
  2. temperatureto cool
  3. filtrationVacuum filtration

Sources & evidence

ORD record
ord-d4009c95c61c42768693b8178016cc97
Source dataset
uspto-grants-1997_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05675004

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes