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Chloroform → Bis(tris(4-t-butylphenyl)sulfonium) perfluorobutane-1,4-disulfonate

HRID 2111496
Notes
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Reaction equation

HRID 2111496 reaction equation
[K+].[F:2][C:3]([F:21])([S:17]([O-:20])(=[O:19])=[O:18])[C:4]([F:16])([F:15])[C:5]([F:14])([F:13])[C:6]([F:12])([F:11])[S:7]([O-:10])(=[O:9])=[O:8].[K+].[OH-].[C:24]([C:28]1[CH:33]=[CH:32][C:31]([S+:34]([C:45]2[CH:50]=[CH:49][C:48]([C:51]([CH3:54])([CH3:53])[CH3:52])=[CH:47][CH:46]=2)[C:35]2[CH:40]=[CH:39][C:38]([C:41]([CH3:44])([CH3:43])[CH3:42])=[CH:37][CH:36]=2)=[CH:30][CH:29]=1)([CH3:27])([CH3:26])[CH3:25].C(Cl)(Cl)Cl>O.CC(C)=O>[F:12][C:6]([F:11])([S:7]([O-:10])(=[O:9])=[O:8])[C:5]([F:14])([F:13])[C:4]([F:15])([F:16])[C:3]([F:2])([F:21])[S:17]([O-:20])(=[O:18])=[O:19].[C:24]([C:28]1[CH:33]=[CH:32][C:31]([S+:34]([C:35]2[CH:40]=[CH:39][C:38]([C:41]([CH3:44])([CH3:43])[CH3:42])=[CH:37][CH:36]=2)[C:45]2[CH:50]=[CH:49][C:48]([C:51]([CH3:53])([CH3:54])[CH3:52])=[CH:47][CH:46]=2)=[CH:30][CH:29]=1)([CH3:25])([CH3:26])[CH3:27].[C:24]([C:28]1[CH:33]=[CH:32][C:31]([S+:34]([C:35]2[CH:40]=[CH:39][C:38]([C:41]([CH3:44])([CH3:43])[CH3:42])=[CH:37][CH:36]=2)[C:45]2[CH:50]=[CH:49][C:48]([C:51]([CH3:53])([CH3:54])[CH3:52])=[CH:47][CH:46]=2)=[CH:30][CH:29]=1)([CH3:25])([CH3:26])[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6212ChloroformHCID 14384439Perfluorobutane-1,4-disulfonic acid potassium saltHCID 87569163Tris(4-t-butylphenyl)sulfonium hydroxide

Product 1

HCID 87388084Bis(tris(4-t-butylphenyl)sulfonium) perfluorobutane-1,4-disulfonate

Reagents, catalysts & solvents 2

HCID 180
Acetone
Solvent
HCID 962WaterSolvent

Procedure

Perfluorobutane-1,4-disulfonic acid potassium salt (2.92 g) in 100 ml water was added to a solution of tris(4-t-butylphenyl)sulfonium hydroxide (7.75 g) in 150 ml of acetone. Chloroform (150 ml) was added and stirred for 5 hours. The chloroform layer was washed several times with water, dried over anhydrous sodium sulfate, filtered, and the filtrate evaporated to an oil stage. Ether was added to the oil and the mixture was stirred vigorously. A white precipitate formed. The mixture was filtered and the recovered precipitate was dried under vacuum, resulting in a white powder; mp 190° C.

Workup

  1. washThe chloroform layer was washed several times with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customthe filtrate evaporated to an oil stage
  5. additionEther was added to the oil
  6. stirringthe mixture was stirred vigorously
  7. customA white precipitate formed
  8. filtrationThe mixture was filtered
  9. customthe recovered precipitate was dried under vacuum
  10. customresulting in a white powder

Sources & evidence

ORD record
ord-fa0325d8cf6c4b4a9b0d31cc5dc19c98
Source dataset
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07521170B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes