Potassium Iodide → 2,4-Bis(4-tert-butylphenyl)-6-(2-hydroxy-4-ethoxycarbonylmethoxyphenyl)-1,3,5-triazine

HRID 1979061Notes

Reaction equation

HRID 1979061 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]([C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][C:28]=3[OH:34])[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46]>CC(C)=O>[C:23]([C:20]1[CH:21]=[CH:22][C:17]([C:15]2[N:16]=[C:11]([C:8]3[CH:7]=[CH:6][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:10][CH:9]=3)[N:12]=[C:13]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])=[CH:29][C:28]=3[OH:34])[N:14]=2)=[CH:18][CH:19]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 1358045042,4-Bis(4-tert-butylphenyl)-6-(2,4-dihydroxyphenyl)-1,3,5-triazine

Product 1

HCID 1357400392,4-Bis(4-tert-butylphenyl)-6-(2-hydroxy-4-ethoxycarbonylmethoxyphenyl)-1,3,5-triazineYield 75%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred mixture of 14 g of 2,4-bis(4-tert-butylphenyl)-6-(2,4-dihydroxyphenyl)-1,3,5-triazine, 10.8 g of anhydrous potassium carbonate, 0.47 g of potassium iodide, and 90 mL of acetone was added 3.7 mL (4,2 g) of ethyl chloroacetate. The mixture was stirred at reflux for 3 hr, and then cooled to room temperature. The solids were removed by filtration and washed with methylene chloride. The product was crystallized from the combined filtrate, washed with cold acetone, and dried in vacuo to give 12.5 g of 2,4-bis(4-tert-butylphenyl)-6-(2-hydroxy-4-ethoxycarbonylmethoxyphenyl)-1,3,5-triazine as a near white powder. The structure was verified by 1H-NMR spectroscopy.

Workup

  1. temperatureat reflux for 3 hr
  2. customThe solids were removed by filtration
  3. washwashed with methylene chloride
  4. customThe product was crystallized from the combined filtrate
  5. washwashed with cold acetone
  6. customdried in vacuo

Sources & evidence

ORD record
ord-6e551cf661d8491b994142a806e78539
Source dataset
uspto-grants-2001_05
Patent number
US06239276B1

Reaction notes

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