Methyl Isobutyl Ketone → 2-(2-Hydroxy-4-octyloxyphenyl)4,6-bis(4-phenoxyphenyl)-1,3,5-triazine

HRID 23850

Reaction equation

HRID 23850 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:17][CH:16]=2)[N:12]=[C:11]([C:28]2[CH:33]=[CH:32][C:31]([O:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:30][CH:29]=2)[N:10]=1.I[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49].C(=O)([O-])[O-].[K+].[K+].CC(CC(C)=O)C>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(Cl)Cl>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:19][CH:20]=2)[N:12]=[C:11]([C:28]2[CH:33]=[CH:32][C:31]([O:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[CH:30][CH:29]=2)[N:10]=1

Participants

7

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 11430Potassium CarbonateHCID 123801-IodooctaneHCID 1356219442-(2,4-Dihydroxyphenyl)-4,6-bis(4-phenoxyphenyl)-1,3,5-triazine

Product 1

HCID 1356219522-(2-Hydroxy-4-octyloxyphenyl)4,6-bis(4-phenoxyphenyl)-1,3,5-triazineYield 57.7%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5 gm 2-(2,4-dihydroxyphenyl)-4,6-bis(4-phenoxyphenyl)-1,3,5-triazine, 2.5 gm 1-iodooctane, 6.6 gm anhydrous potassium carbonate, 0.5 gm Aliquat 336 and 25 ml MIBK was heated to reflux for 3 hr. The reaction mixture was cooled to room temperature, diluted with methylene chloride, filtered through Celite. The filtrate was concentrated under reduced pressure. The residue thus obtained was passed through a silica gel column. The material thus obtained was crystallized with acetone to give 3.5 gm of pure 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(4-phenoxyphenyl)-1,3,5-triazine.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hr
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue thus obtained
  6. customThe material thus obtained
  7. customwas crystallized with acetone

Sources & evidence

ORD record
ord-8826021f3fe142c0834142035b884578
Source dataset
uspto-grants-2005_02
Patent number
US06855269B2

Linked notes

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