4-Chlorophenol → 5-Chloro-2-hydroxybenzene-1-sulfonyl chloride

HRID 1020456Notes

Reaction equation

HRID 1020456 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Cl:9][S:10](O)(=[O:12])=[O:11]>O>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[S:10]([Cl:9])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 46844-ChlorophenolHCID 24638Chlorosulfonic acid

Product 1

HCID 3043845-Chloro-2-hydroxybenzene-1-sulfonyl chlorideYield 30.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

4-Chlorophenol (4 g, 31.25 mmol) was added in portions to chlorosulfonic acid (10.3 mL, 156 mmol) while cooling in an ice bath. The resulting solution was stirred at 25° C. for 20 hrs. This was then added drop-wise to ice and water resulting in an emulsion. This was extracted with CHCl3, dried (Na2SO4) and concentrated in vacuo. Heptane was added and evaporated and replaced with cyclohexane. The resulting mixture was filtered and concentrated to give the title compound as an oil (2.16 g).

Workup

  1. temperaturewhile cooling in an ice bath
  2. extractionThis was extracted with CHCl3
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. additionHeptane was added
  6. customevaporated
  7. filtrationThe resulting mixture was filtered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5c11506c44324cac99d859a7282f8f6d
Source dataset
uspto-grants-2014_05
Patent number
US08716345B2

Reaction notes

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