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

HRID 1635591Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:18]=3)[N:14]=[C:13](Cl)[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:28]1([CH:35]=[CH:34][CH:33]=[C:31]([OH:32])[CH:30]=1)[OH:29].[Cl-].[Al+3].[Cl-].[Cl-]>ClC1C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:18]=3)[N:14]=[C:13]([C:33]3[CH:34]=[CH:35][C:28]([OH:29])=[CH:30][C:31]=3[OH:32])[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

To a 2-neck flask equipped with a reflux condenser, an argon inlet, a magnetic stirring bar and a glass stopper was introduced 3.79 g of 2,4-bis(4-tert-butylphenyl)-6-chloro-1,3,5-triazine of example 1. To it was added 30 mL of chlorobenzene, 1.21 g of resorcinol and 2 g of aluminum chloride at room temperature. The reaction mixture was heated at 85° C. for 6 hr. The heating was discontinued and the reaction was allowed to cool to room temperature. To it was then added 5% ice-cold aq. HCl, and the mixture concentrated under reduced pressure. The residue was washed with water and dried to give 4.4 g of a product characterized to be 2,4-bis(4-tert-butylphenyl)-6-(2,4-dibydroxyphenyl)-1,3,5-triazine.

Workup

customTo a 2-neck flask equipped with a reflux condenser, an argon inlet, a magnetic stirring bar
temperatureto cool to room temperature
concentrationthe mixture concentrated under reduced pressure
washThe residue was washed with water
customdried

Sources & evidence

ORD record: ord-43ce290fb6d34381a56fe5f58a794a5b
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06509399B2

Reaction notes

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