1-Propanesulfonic acid, 1,1,2,3,3,3-hexafluoro- → Tris-(4-hydroxyphenyl) sulfonium 3,3,3,2,1,1-hexafluoropropane sulfonate

HRID 277682

Reaction equation

HRID 277682 reaction equation
[F:1][C:2]([F:13])([F:12])[CH:3]([F:11])[C:4]([F:10])([F:9])[S:5]([O-:8])(=[O:7])=[O:6].C([O:18][C:19]1[CH:24]=[CH:23][C:22]([S+:25]([C:37]2[CH:42]=[CH:41][C:40]([O:43]CCCC)=[CH:39][CH:38]=2)[C:26]2[CH:31]=[CH:30][C:29]([O:32]CCCC)=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)CCC.FC(F)(F)C(F)C(F)(F)S(O)(=O)=O>C(O)C>[F:13][C:2]([F:1])([F:12])[CH:3]([F:11])[C:4]([F:9])([F:10])[S:5]([O-:8])(=[O:6])=[O:7].[OH:18][C:19]1[CH:24]=[CH:23][C:22]([S+:25]([C:37]2[CH:42]=[CH:41][C:40]([OH:43])=[CH:39][CH:38]=2)[C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 97946281-Propanesulfonic acid, 1,1,2,3,3,3-hexafluoro-HCID 86757888HCID 86757888, compound

Product 1

HCID 88189245Tris-(4-hydroxyphenyl) sulfonium 3,3,3,2,1,1-hexafluoropropane sulfonateYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 56.8 g (0.08 mol) of tris-(4-butoxyphenyl) sulfonium 3,3,3,2,1,1-hexafluoropropane sulfonate and 1.86 g (0.008 mol) of 3,3,3,2,1,1-hexafluoropropane sulfonic acid in 200 ml of ethanol was refluxed for 8 hours with stirring. After evaporation of the solvent, the obtained crude product of tris-(4-hydroxyphenyl) sulfonium 3,3,3,2,1,1-hexafluoropropane 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 31.8 g (yield 45%) of analytically pure tris-(4-t-butoxycarbonylmethoxyphenyl) sulfonium 3,3,3,2,1,1-hexafluoropropane sulfonate. The melting point of the product was 78° C. The 1H-NMR spectrum gave the following signals (CDCl3): δ=1.45 (s, 27H), 4.56 (s, 6H), 5.20-5.56 (d[m], 1H), 7.10-7.13 (d, 6H), 7.55-7.60 (d, 6H).

Workup

  1. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-86ac58e9ac2348e5aa9173eaa42a7c6c
Source dataset
uspto-grants-2002_03
Patent number
US06358665B1

Linked notes

Loading…