2-Nitrophenol → 4-Hydroxy-3-nitrobenzene-1-sulfonyl chloride

HRID 216307Notes

Reaction equation

HRID 216307 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[N+:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])([O-:8])=[O:7]>>[OH:15][C:10]1[CH:11]=[CH:12][C:13]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:14][C:9]=1[N+:6]([O-:8])=[O:7]

Participants

3

Reactant 2

HCID 69472-NitrophenolHCID 24638Chlorosulfonic acid

Product 1

HCID 36704794-Hydroxy-3-nitrobenzene-1-sulfonyl chlorideYield 64%

Conditions

Temperature
60 °C

Procedure

To a solution of chlorosulfonic acid (12.0 mL, 180 mmol) at 0° C. was added 2-nitrophenol (8.35 g, 60.0 mmol) in small portions over 1 h. The reaction was heated to 60° C. for 20 minutes and allowed to stir for 18 h at 25° C. The reaction was quenched by pouring it into 100 g of ice. The reaction was extracted with chloroform (3×), washed with cold water (2×), dried over MgSO4, filtered, and concentrated to give 9.06 g (64%) of the title compound.

Workup

  1. customThe reaction was quenched
  2. additionby pouring it into 100 g of ice
  3. extractionThe reaction was extracted with chloroform (3×)
  4. washwashed with cold water (2×)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-87a57751c10b4acda31417e824a1f39b
Source dataset
uspto-grants-2012_06
Patent number
US08193227B2

Reaction notes

Loading…