Water → 4-Hydroxybenzene-1-sulfonyl chloride

HRID 1768075Notes

Reaction equation

HRID 1768075 reaction equation
O.O.[OH:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([O-:13])(=O)=[O:11])=[CH:6][CH:5]=1.[Na+].O.S(Cl)([Cl:18])=O.CN(C=O)C>C1(C)C=CC=CC=1>[OH:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([Cl:18])(=[O:13])=[O:11])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 23666329Sodium P-phenolsulfonate dihydrate

Product 1

HCID 114240934-Hydroxybenzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

5 g (21.5 mmol) sodium 4-hydroxy-benzenesulfonate dihydrate were suspended in 50 ml toluene and refluxed for 2 hours using a Dean-Stark trap (a water separator used in chemical reactions). The solvent was evaporated, replaced by 12.8 g (108 mmol) thionyl chloride and 160 mg DMF and the mixture stirred for 4 hours at 60° C. and over night at room temperature. After evaporation, the residue was quenched with ice water, extracted thrice with dichloromethane and the extracts died and evaporated. Yield 4.78 g (quant.) raw product as white gum.

Workup

  1. temperaturerefluxed for 2 hours
  2. customThe solvent was evaporated
  3. customAfter evaporation
  4. customthe residue was quenched with ice water
  5. extractionextracted thrice with dichloromethane
  6. customevaporated

Sources & evidence

ORD record
ord-347fc0511d42480c80fa2ceb3014e45a
Source dataset
uspto-grants-2007_06
Patent number
US07235574B2

Reaction notes

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