Water → HCID 22023911, compound

HRID 900517Notes

Reaction equation

HRID 900517 reaction equation
[Cl-].[OH:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([S+:10]([CH3:12])[CH3:11])=[CH:5][C:4]=1[CH3:13].O.[F:15][C:16]([F:31])([S:27]([O-:30])(=[O:29])=[O:28])[C:17]([F:26])([F:25])[C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20].[K+]>CC(C)=O>[S:27]([C:16]([C:17]([C:18]([C:19]([F:20])([F:21])[F:22])([F:23])[F:24])([F:26])[F:25])([F:31])[F:15])([O-:30])(=[O:29])=[O:28].[OH:2][C:3]1[C:4]([CH3:13])=[CH:5][C:6]([S+:10]([CH3:11])[CH3:12])=[CH:7][C:8]=1[CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 22251526HCID 22251526, compoundHCID 23675274Potassium perfluorobutanesulfonate

Product 1

HCID 22023911HCID 22023911, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

15.01 g of 4-Hydroxy-3,5-dimethyl phenyl dimethyl sulphonium chloride, 300 g water, and 23.35 g of potassium perfluorobutane sulfonate in 100 ml acetone were added to a flask. The resulting mixture was stirred for 2 hours at room temperature. The solution was then extracted with chloroform, washed with water, dried over sodium sulphate and filtered. The solution was concentrated and drowned into ether; a precipitate was formed, filtered and dried in the vacuum dryer at less than 40° C., yielding 4-hydroxy-3,5-dimethyl phenyl dimethyl sulphonium nonaflate, 23.9 g (71.9%). The solid product gave the following analytical results: 1H NMR (DMSO-d6), 2.35 (s, 6H, 2CH3); 3.5 (s, 6H, 2CH3); 7.80 (s, 2H, aromatic), mp 98° C.

Workup

  1. extractionThe solution was then extracted with chloroform
  2. washwashed with water
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationThe solution was concentrated
  6. customa precipitate was formed
  7. filtrationfiltered
  8. customdried in the vacuum dryer at less than 40° C.

Sources & evidence

ORD record
ord-f3ec16f237504cdf87fb22c5266134bb
Source dataset
uspto-grants-2008_04
Patent number
US07358408B2

Reaction notes

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