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Sodium Hydroxide → 2-{4,6-bis-[4-(2-Ethylhexyloxy)phenyl]-s-triazin-2-yl}-5-(2-ethylhexyloxy)phenol

HRID 232898
Notes
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Reaction equation

HRID 232898 reaction equation
[CH2:1]([CH:3]([CH2:41][CH2:42][CH2:43][CH3:44])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]([CH2:31][CH3:32])[CH2:27][CH2:28][CH2:29][CH3:30])=[CH:20][CH:19]=3)[N:15]=[C:14]([C:33]3[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][C:34]=3[OH:40])[N:13]=2)=[CH:8][CH:7]=1)[CH3:2].[OH-].[Na+].Br[CH2:48][CH:49]([CH2:52][CH2:53][CH2:54][CH3:55])[CH2:50][CH3:51]>COCCO>[CH2:1]([CH:3]([CH2:41][CH2:42][CH2:43][CH3:44])[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]([CH2:31][CH3:32])[CH2:27][CH2:28][CH2:29][CH3:30])=[CH:20][CH:19]=3)[N:15]=[C:14]([C:33]3[CH:38]=[CH:37][C:36]([O:39][CH2:48][CH:49]([CH2:50][CH3:51])[CH2:52][CH2:53][CH2:54][CH3:55])=[CH:35][C:34]=3[OH:40])[N:13]=2)=[CH:10][CH:11]=1)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 868042-Ethylhexyl bromideHCID 1355632624-{4,6-Bis[4-(2-ethylhexyloxy)phenyl]-s-triazin-2-yl}-1,3-dihydroxybenzene

Product 1

HCID 1355762652-{4,6-bis-[4-(2-Ethylhexyloxy)phenyl]-s-triazin-2-yl}-5-(2-ethylhexyloxy)phenolYield 101.5%

Reagents, catalysts & solvents 1

HCID 8019
2-Methoxyethanol
Solvent
2×

Procedure

A 1 l sulfonating flask equipped with stirrer, condenser, internal thermometer and dropping funnel is charged at 80° C. with 83.7 g (0.14 mol) of 4-{4,6-bis[4-(2-ethylhexyloxy)phenyl]-s-triazin-2-yl}-1,3-dihydroxybenzene together with 500 ml of methylcellosolve. 18.1 g of 30% sodium hydroxide solution (0.16 mol) are added, stirring is continued for 15 minutes, and a solution of 31.4 g (0.16 mol) of 3-bromomethylheptane and 30 ml of methylcellosolve is then added dropwise over a period of 30 minutes. After 24 hours of stirring at 110° C., alkylation is complete (thin-layer chromatogram). The mixture is evaporated to dryness in vacuo, the residue is dissolved in 500 ml of toluene, the resulting solution is filtered, and the filtrate is extracted with water. The organic phase is dried over sodium sulfate and the solvent is distilled off to give 100.9 g of a red-brown oil. The crude product is dissolved in 200 ml of 97.5:2.5 toluene/ethyl acetate and purified by chromatographing it through silica gel (10 cm×40 cm). This gives 79.4 g (80% of theory) of the compound of the formula ##STR26## as a honey-like, red-brown resin.

Workup

  1. customequipped with stirrer, condenser
  2. stirringAfter 24 hours of stirring at 110° C.
  3. customThe mixture is evaporated to dryness in vacuo
  4. dissolutionthe residue is dissolved in 500 ml of toluene
  5. filtrationthe resulting solution is filtered
  6. extractionthe filtrate is extracted with water
  7. dry with materialThe organic phase is dried over sodium sulfate
  8. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-7a638ddd8026439b90a6abd90a91b00e
Source dataset
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05591850

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes