Oxalyl chloride → 4-Hydroxybenzene-1-sulfonyl chloride

HRID 1966130Notes

Reaction equation

HRID 1966130 reaction equation
[Na].O.O.[OH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([OH:14])(=O)=[O:12])=[CH:7][CH:6]=1.C(Cl)(=O)C([Cl:18])=O>CN(C)C=O.ClCCl>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([Cl:18])(=[O:14])=[O:12])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 5360545SodiumHCID 865908324-Hydroxybenzene-1-sulfonic acid dihydrate

Product 1

HCID 114240934-Hydroxybenzene-1-sulfonyl chlorideYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

A solution of 7 g (30 mmol) of the sodium salt of 4-hydroxybenzenesulfonic acid dihydrate in 40 ml of dimethylformamide is added dropwise to a solution of 15.5 ml (181 mmol) of oxalyl chloride in 120 ml of dichloromethane cooled to −30° C. The reaction medium is slowly brought back to ambient temperature and then stirred at ambient temperature for 18 h. After the addition of 200 ml of ice, the reaction medium is extracted with ethyl acetate. The organic phase is washed with water and with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated. 6.2 g (100%) of 4-hydroxybenzenesulfonyl chloride are obtained in the form of a colorless oil.

Workup

  1. customis slowly brought back to ambient temperature
  2. extractionthe reaction medium is extracted with ethyl acetate
  3. washThe organic phase is washed with water and with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ac86793eb3624310ac8d6ece65861839
Source dataset
uspto-grants-2013_04
Patent number
US08420632B2

Reaction notes

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