Potassium Carbonate → HCID 135740037, compound

HRID 1635592Notes

Reaction equation

HRID 1635592 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]=[C:31]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:30]([OH:39])=[CH:29][C:28]=3[OH:40])[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].I[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49].C(=O)([O-])[O-].[K+].[K+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(C(C)=O)C(C)C>[C:23]([C:20]1[CH:19]=[CH:18][C:17]([C:15]2[N:16]=[C:11]([C:8]3[CH:7]=[CH:6][C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])=[CH:10][CH:9]=3)[N:12]=[C:13]([C:27]3[CH:32]=[C:31]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:30]([O:39][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])=[CH:29][C:28]=3[OH:40])[N:14]=2)=[CH:22][CH:21]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 123801-IodooctaneHCID 135804512HCID 135804512, compound

Product 1

HCID 135740037HCID 135740037, compound

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
117.5 °C

Procedure

A stirred mixture of 2,4-bis(4-tert-butylphenyl)-6-(2,4-dihydroxy-5-hexylphenyl)-1,3,5-triazine, 5 g of 1-iodooctane, 1 g of Aliquat® 336 (tricaprylmethylammonium chloride), 14 g anhydrous potassium carbonate, and 200 mL methyl isobutyl ketone (MIBK) was heated at 115-120° C. for 5 hr, and then allowed to cool to room temperature. The mixture was extracted with methylene chloride and the combined methylene chloride extracts were concentrated under reduced pressure. The resulting semi-solid residue was recrystallized from acetone to give 12 g of 2,4-bis(4-tert-butylphenyl)-6-(2-hydroxy-4-octyloxy-5-hexylphenyl)-1,3,5-triazine as a yellow solid in 97% purity as determined by HPLC (area % at 290 nm). A second recrystallization from acetone yielded an analytical sample (100% purity by HPLC).

Workup

  1. temperatureto cool to room temperature
  2. extractionThe mixture was extracted with methylene chloride
  3. concentrationthe combined methylene chloride extracts were concentrated under reduced pressure
  4. customThe resulting semi-solid residue was recrystallized from acetone

Sources & evidence

ORD record
ord-dcca39627b674a4cb7c6eefa0d8c9e90
Source dataset
uspto-grants-2003_01
Patent number
US06509399B2

Reaction notes

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