4-Toluenesulfonyl chloride → 2,2-Bis-(3-nitro-4-tosyloxyphenyl)hexafluoropropane

HRID 1086326Notes

Reaction equation

HRID 1086326 reaction equation
[OH-:1].[K+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([N+:26]([O-:28])=[O:27])[CH:20]=2)([C:15]([F:18])([F:17])[F:16])[C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[N+:29]([O-:31])=[O:30].[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1>C(Cl)Cl>[N+:26]([C:21]1[CH:20]=[C:19]([C:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][S:38]([C:35]3[CH:36]=[CH:37][C:32]([CH3:42])=[CH:33][CH:34]=3)(=[O:39])=[O:1])=[C:5]([N+:29]([O-:31])=[O:30])[CH:6]=2)([C:15]([F:18])([F:16])[F:17])[C:11]([F:13])([F:12])[F:14])[CH:24]=[CH:23][C:22]=1[O:25][S:38]([C:35]1[CH:36]=[CH:37][C:32]([CH3:42])=[CH:33][CH:34]=1)(=[O:40])=[O:39])([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 111336832,2-Bis(3-nitro-4-hydroxyphenyl)hexafluoropropane

Product 1

HCID 142050432,2-Bis-(3-nitro-4-tosyloxyphenyl)hexafluoropropaneYield 58.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

11.5 g (0.205 mol) of potassium hydroxide are added to a solution of 42.6 g (0.1 mol) of 2,2-bis-(4-hydroxy-3-nitrophenyl) -hexafluoropropane and 39.1 g (0.205 mol) of p-toluenesulfonyl chloride in 300 ml of methylene chloride. The reaction mixture is then stirred at room temperature for five hours, in the course of which it turns an orange-yellow color. After precipitated potassium chloride (16 g) has been removed, the filtrate is dried over MgSO4. Removing the solvent and recrystallizing from toluene gives 43 g of 2,2-bis-(3-nitro-4-tosyloxyphenyl)-hexafluoropropane. Yield 58%; m.p. 206-208° C.

Workup

  1. customAfter precipitated potassium chloride (16 g)
  2. customhas been removed
  3. dry with materialthe filtrate is dried over MgSO4
  4. customRemoving the solvent
  5. customrecrystallizing from toluene

Sources & evidence

ORD record
ord-8278ea6522ee41d29c1029fdc085fc27
Source dataset
uspto-grants-1991_07
Patent number
US05028728

Reaction notes

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