Acetone → HCID 87490629, compound

HRID 2244135Notes

Reaction equation

HRID 2244135 reaction equation
[F:1][C:2]([F:17])([S:13]([O-:16])(=[O:15])=[O:14])[C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6].[OH:18][C:19]1[CH:24]=[CH:23][C:22]([S+:25]([C:32]2[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:21][CH:20]=1.C[C:40]([CH3:42])=[O:41].C(=O)([O-])[O-].[K+].[K+].[C:49](OC(=O)C)(=[O:51])[CH3:50]>CCOCC.ClCCl.O>[F:17][C:2]([F:1])([S:13]([O-:16])(=[O:15])=[O:14])[C:3]([F:11])([F:12])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6].[C:49]([O:18][C:19]1[CH:24]=[CH:23][C:22]([S+:25]([C:32]2[CH:33]=[CH:34][C:35]([O:38][C:40](=[O:41])[CH3:42])=[CH:36][CH:37]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)(=[O:51])[CH3:50]

Participants

8

Reactant 4

HCID 180AcetoneHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 23133152HCID 23133152, compound

Product 1

HCID 87490629HCID 87490629, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

Bis[4-hydroxylphenyl]phenysulfonium perfluorobutanesulfonate (10 g) and acetone were placed into a reaction vessel equipped with an agitator, a thermometer, a reflux condenser, and a tube for introducing nitrogen gas into the vessel. Under a nitrogen blanket, 4.6 g of potassium carbonate was added to the reaction vessel and the mixture was stirred for an hour. Acetic anhydride 3.43 gram was added and stirred overnight at room temperature. Dichloromethane (150 ml) and water were added to the reaction vessel and the mixture was stirred for 2 hours. The mixture was then placed into a separatory funnel and the organic (dichloromethane) layer was retained. The dichloromethane layer was washed several times with water, dried over anhydrous sodium sulfate, filtered, and the remaining volatile materials were evaporated to leave an oil. Ether was added to the oil and the mixture was stirred vigorously. A very sticky solid was obtained.

Workup

  1. customequipped with an agitator
  2. additiona thermometer, a reflux condenser, and a tube for introducing nitrogen gas into the vessel
  3. stirringstirred overnight at room temperature
  4. stirringthe mixture was stirred for 2 hours
  5. customThe mixture was then placed into a separatory funnel
  6. washThe dichloromethane layer was washed several times with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customthe remaining volatile materials were evaporated
  10. customto leave an oil
  11. stirringthe mixture was stirred vigorously
  12. customA very sticky solid was obtained

Sources & evidence

ORD record
ord-64e7cbdb206146d3b31cf622fbd1a0cb
Source dataset
uspto-grants-2010_03
Patent number
US07678528B2

Reaction notes

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