Biphenyl → (1,1'-Biphenyl)-4-sulfonic acid

HRID 29492

Reaction equation

HRID 29492 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[S:14]([OH:17])(=[O:16])=[O:15]>C(Cl)(Cl)Cl>[C:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][C:4]([S:14]([OH:17])(=[O:16])=[O:15])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7095BiphenylHCID 24638Chlorosulfonic acid

Product 1

HCID 16673(1,1'-Biphenyl)-4-sulfonic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Biphenyl (46.3 g, 0.3 mol) was dissolved in 500 ml of chloroform. The solution was cooled in an ice/water bath. Chlorosulfonic acid (19.9 ml, 1 eq) was added dropwise over 30 min. The ice/water bath was removed and the reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered and the solid was washed with CHCl3 to provide 41.2 g of biphenyl-4-sulfonic acid as a white solid.

Workup

  1. temperatureThe solution was cooled in an ice/water bath
  2. customThe ice/water bath was removed
  3. filtrationThe reaction mixture was filtered
  4. washthe solid was washed with CHCl3

Sources & evidence

ORD record
ord-f079c72dfa1340118c5900b0f53c394f
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Linked notes

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