Phenol → 4-Hydroxybenzene-1-sulfonyl chloride

HRID 1744828Notes

Reaction equation

HRID 1744828 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[C:6]1([OH:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(Cl)Cl>[OH:12][C:6]1[CH:11]=[CH:10][C:9]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 996PhenolHCID 24638Chlorosulfonic acid

Product 1

HCID 114240934-Hydroxybenzene-1-sulfonyl chlorideYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To chlorosulfonic acid (248 mL, 3.37 mol) cooled to −3° C. was added dropwise a solution of phenol (70 g, 0.744 mot) in 250 mL of anhydrous methylene chloride over a period of 1 hour under argon gas. The mixture was warmed to rt over 1 h and was stirred at rt for 1.5 h. The mixture was poured over ice, stirred for 30 min, and was extracted with methylene chloride (4×2 L). The resulting organic layer was dried over MgSO4 and concentrated in vacuo to yield 4-hydroxybenzenesulfonyl chloride as a sticky brown solid (41.49 g, 29%): 1H NMR (400 MHz, d6-DMSO) δ 7.29–7.38 (d, 2 H), 6.58–6.69 (d, 2 H).

Workup

  1. additionThe mixture was poured over ice
  2. stirringstirred for 30 min
  3. extractionwas extracted with methylene chloride (4×2 L)
  4. dry with materialThe resulting organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb41718524424a15a3e20b0fb54635ac
Source dataset
uspto-grants-2006_03
Patent number
US07019008B2

Reaction notes

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