HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1595949
Notes
Print preview

Reaction equation

HRID 1595949 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent

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-85063857d93140d2a3d830d7aa231f03
Source dataset
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06288188B1

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes