Thionyl Chloride → 4-Hydroxybenzene-1-sulfonyl chloride

HRID 1518775Notes

Reaction equation

HRID 1518775 reaction equation
S(Cl)([Cl:3])=O.[OH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([O-:15])(=O)=[O:13])=[CH:8][CH:7]=1.[Na+]>CN(C)C=O>[OH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([Cl:3])(=[O:15])=[O:13])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 4379756Sodium 4-hydroxybenzenesulfonate

Product 1

HCID 114240934-Hydroxybenzene-1-sulfonyl chlorideYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Thionyl chloride (44.3 mL, 604 mmol, and 6.91 Eq) and N,N-dimethylformamide (DMF) (1 mL) were added to sodium 4-hydroxybenzenesulfonate (20.3 g, 87.2 mmol, and 1.00 Eq) under an argon atmosphere, and the mixture was stirred under reflux at 60° C. for 4 hours. The resultant mixture was cooled to room temperature and ice (160 g) was added thereto. The mixture was stirred and the water layer was extracted with dichloromethane (1×60 mL, 2×40 mL). The obtained organic layer was washed with ice water (40 mL) and dried with sodium sulfate. The solvent was removed by an evaporator and 4-hydroxybenzene sulfonyl chloride (10.4 g, 53.8 mmol, 62%) was obtained as oil.

Workup

  1. stirringThe mixture was stirred
  2. extractionthe water layer was extracted with dichloromethane (1×60 mL, 2×40 mL)
  3. washThe obtained organic layer was washed with ice water (40 mL)
  4. dry with materialdried with sodium sulfate
  5. customThe solvent was removed by an evaporator

Sources & evidence

ORD record
ord-57bdbd237f904c08a5da66d27730941a
Source dataset
uspto-grants-2015_07
Patent number
US09073284B2

Reaction notes

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