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

HRID 1899674Notes

Reaction equation

HRID 1899674 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([S:7](O)(=[O:9])=[O:8])=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:19])=O>>[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([S:7]([Cl:19])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 16673(1,1'-Biphenyl)-4-sulfonic acidHCID 24813Phosphorus oxychloride

Product 1

HCID 74192(1,1'-Biphenyl)-4-sulphonyl chloride

Procedure

4-Biphenylsulfonic acid (3.0 g, 12.8 mmol) was heated at 70° C. with phosphorus oxychloride (1.30 ml, 14.0 mol) for 2 h. Excess phosphorus oxychloride was removed under reduced pressure. The residue was decomposed with ice water and extracted with ethyl acetate. The extract was washed with 5% sodium bicarboinate solution, dried over anhydrous magnesium sulfate and concentrated to yield 2.9 crude 4-biphenylsulfonyl chloride.

Workup

  1. customExcess phosphorus oxychloride was removed under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with 5% sodium bicarboinate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4ea51bc9e1cb43a0b86164a6487acf06
Source dataset
uspto-grants-1996_11
Patent number
US05571821

Reaction notes

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