Ethanol → 3,3'-(1,4-Phenylene)bis(2,4,5-triphenylcyclopentadienone)

HRID 1739357Notes

Reaction equation

HRID 1739357 reaction equation
[C:1]1([CH2:7][C:8]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1([C:23](=O)[C:24]([C:26]2[CH:31]=[CH:30][C:29]([C:32](=O)[C:33]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=O)=[CH:28][CH:27]=2)=O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:43]([OH:45])[CH3:44].[OH-].[K+]>O>[C:29]1([C:32]2[C:33]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:43](=[O:45])[C:44]=2[C:12]2[CH:11]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:30]=[CH:31][C:26]([C:24]2[C:23]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8](=[O:9])[C:10]=2[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 75931,3-Diphenyl-2-propanoneHCID 14797Potassium Hydroxide2×HCID 1379051,4-Bis(phenylglyoxaloyl)benzene

Product 1

HCID 28328333,3'-(1,4-Phenylene)bis(2,4,5-triphenylcyclopentadienone)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,3-Diphenylacetone (1.23 g, 0.00584 mol), 1,4-bis(phenylglyoxaloyl)benzene, commercially available as Bis-PGB from Ken Seika Corporation (1.000 g, 0.00292 mol) and ethanol (50 mL) are added to a 100 mL 3-necked round bottom flask fitted with a reflux condenser/nitrogen inlet. The reaction mixture is heated to reflux and an aqueous KOH solution (0.112 g, 0.002 mol) in water (2.25 mL) is added. Additional KOH is added until the solution turns dark and stays dark. The mixture is refluxed for 45 minutes and then allowed to cool. A dark solid which precipitates is collected by filtration and analyzed by 1H-NMR, 13C-NMR, HPLC and FT-IR. All data is consistent with the formation of Compound B.

Workup

  1. customfitted with a reflux condenser/nitrogen inlet
  2. temperatureThe reaction mixture is heated
  3. temperatureto reflux
  4. temperatureThe mixture is refluxed for 45 minutes
  5. temperatureto cool
  6. customA dark solid which precipitates
  7. filtrationis collected by filtration

Sources & evidence

ORD record
ord-dbfc25c87c6a4247b694288187029c9f
Source dataset
uspto-grants-1999_10
Patent number
US05965679

Reaction notes

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