Potassium Iodide → 2-Phenyl-4-(2-hydroxy-4-n-hexyloxy-phenyl)-6-[2-hydroxy-4-(11-hydroxy-undecyloxy)-phenyl]-1,3,5-triazine

HRID 1735912Notes

Reaction equation

HRID 1735912 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=3[OH:20])[N:10]=[C:9]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=3[OH:28])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].Br[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][OH:43].[I-].[K+]>C(O)COCCO.COC>[C:1]1([C:7]2[N:8]=[C:9]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH2:5][CH2:6][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:23][C:22]=3[OH:28])[N:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][OH:43])=[CH:15][C:14]=3[OH:20])[N:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 14797Potassium Hydroxide2×HCID 7416311-Bromo-1-undecanolHCID 1358454012,4-Bis-(2,4-dihydroxyphenyl)-6-phenyl-s-triazine

Product 1

HCID 1362052792-Phenyl-4-(2-hydroxy-4-n-hexyloxy-phenyl)-6-[2-hydroxy-4-(11-hydroxy-undecyloxy)-phenyl]-1,3,5-triazineYield 71.7%

Reagents, catalysts & solvents 1

HCID 212256572-(2-Hydroxyethoxy)ethanol;methoxymethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 37.3 g of 2-phenyl-4,6-bis-(2,4-dihydroxy-phenyl)-1,3,5-triazine (0.100 moles ), 6.6 g of powdered KOH (Fluka, >85%, 0.100 moles), 25.9 g of 11-bromo-1-undecanol(Fluka, 97%, 0.103 moles), and 0.6 g (3.6 mmoles) of Potassium iodide (Merck, 99.5% ) in 160 mL of diethyleneglycol-dimethyl ether (Diglyme, Fluka, 99% ) is heated under stirring at 110° C. for 4 hours 30 min. After cooling to 50° C., there are added 6.6 g (0.100 moles) of powdered KOH (Fluka, >85% ) and 17.0 g (0.103 moles) of n-bromohexane (Fluka, 98%). The mixture is heated at 105° C. under stirring for 14 hours. The mixture is filtered hot and the filtrate evaporated (rotovapor). The product is submitted to a column chromatography [Kieselgel 60, 230-400 mesh; 10 cm diameter; h=30 cm; eluant: CH2Cl2 ]. The first eluted product is the di-hexyl-derivative, the second eluted product eluted is the desired title product and the third product is the product dialkylated by two groups 11-hydroxyundecyl. After drying at 60° C./60 mmHg for 24 hours, there are obtained 22.5 g (35.8% yield) of 2-phenyl-4-(2-hydroxy-4-n-hexyloxy-phenyl)-6-[2-hydroxy-4-(11-hydroxy-undecyloxy)-phenyl]-1,3,5-triazine, as a pale yellow solid, F. 96°-99° C.

Workup

  1. temperatureis heated
  2. temperatureAfter cooling to 50° C.
  3. temperatureThe mixture is heated at 105° C.
  4. stirringunder stirring for 14 hours
  5. filtrationThe mixture is filtered hot
  6. customthe filtrate evaporated (rotovapor)
  7. washthe second eluted product eluted
  8. customAfter drying at 60° C./60 mmHg for 24 hours

Sources & evidence

ORD record
ord-8c504eb6bc8d423dad979a1d8de93c1e
Source dataset
uspto-grants-1996_07
Patent number
US05538840

Reaction notes

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