Perfluorobutanesulfonic acid → Tris-(4-hydroxyphenyl) sulfonium nonafluorobutane sulfonate

HRID 277692

Reaktionsgleichung

Reaktionsgleichung von HRID 277692
[F:1][C:2]([F:17])([F:16])[C:3]([F:15])([F:14])[C:4]([F:13])([F:12])[C:5]([F:11])([F:10])[S:6]([O-:9])(=[O:8])=[O:7].C([O:22][C:23]1[CH:28]=[CH:27][C:26]([S+:29]([C:41]2[CH:46]=[CH:45][C:44]([O:47]CCCC)=[CH:43][CH:42]=2)[C:30]2[CH:35]=[CH:34][C:33]([O:36]CCCC)=[CH:32][CH:31]=2)=[CH:25][CH:24]=1)CCC.FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(O)(=O)=O>C(O)C.CN(C)C=O>[F:17][C:2]([F:1])([F:16])[C:3]([F:14])([F:15])[C:4]([F:12])([F:13])[C:5]([F:10])([F:11])[S:6]([O-:9])(=[O:8])=[O:7].[OH:22][C:23]1[CH:28]=[CH:27][C:26]([S+:29]([C:41]2[CH:46]=[CH:45][C:44]([OH:47])=[CH:43][CH:42]=2)[C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=2)=[CH:25][CH:24]=1

Komponenten

5

Edukt 2

HCID 67815Perfluorobutanesulfonic acidHCID 22599127Tris-(4-butoxyphenyl) sulfonium nonafluorobutane sulfonate

Produkt 1

HCID 22023915Tris-(4-hydroxyphenyl) sulfonium nonafluorobutane sulfonateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 62.2 g (0.08 mol) of tris-(4-butoxyphenyl) sulfonium nonafluorobutane sulfonate and 2.40 g (0.008 mol) of nonafluorobutane sulfonic acid in 200 ml of ethanol was refluxed for 8 hours with stirring. After evaporation of the solvent, the crude product of tris-(4-hydroxyphenyl) sulfonium nonafluorobutane sulfonate (yield about 100%) was dissolved in 160 g of N,N-dimethylformamide and reacted with 55.4 g (0.40 mol) of anhydrous potassium carbonate and 60.3 g (0.40 mol) of t-butyl chloroacetate at 80° C. for 3 hours. The cooled reaction mixture was poured into 700 ml of water and extracted with dichloromethane. The organic phase was washed with water and dried. The solvent was removed. The oily residue was purified by column chromatography on silica gel using a dichloromethane and methanol as the eluent. The white product was collected to yield 34.4 g (yield 45%) of analytically pure tris-(4-t-butoxycarbonylmethoxyphenyl) sulfonium nonafluorobutane sulfonate. The 1H-NMR spectrum gave the following signals (CDCl3): δ=1.45 (s, 27H), 4.76 (s, 6H), 7.15-7.18 (d, 6H). 7.74-7.87 (d, 6H).

Aufarbeitung

  1. customAfter evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-fea2f148909445f5b0188d08df423869
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06358665B1

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