Phenyl chloroformate → Benzenesulfonic acid, 4-[(chlorocarbonyl)oxy]-

HRID 704057Notes

Reaction equation

HRID 704057 reaction equation
[S:1]([O-:5])([O-])(=[O:3])=[O:2].[Ca+2].S(=O)(=O)=O.[Cl:11][C:12]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:13].ClC([O-])=O>C(Cl)Cl>[Cl:11][C:12]([O:14][C:15]1[CH:20]=[CH:19][C:18]([S:1]([OH:5])(=[O:3])=[O:2])=[CH:17][CH:16]=1)=[O:13]

Participants

6

Reactant 4

HCID 15891Phenyl chloroformateHCID 24497Calcium SulfateHCID 24682Sulfur trioxideHCID 21226386Carbonochloridate

Product 1

HCID 10889932Benzenesulfonic acid, 4-[(chlorocarbonyl)oxy]-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 100 mL 3-necked round bottom flask equipped with a magnetic stirrer, addition funnel topped with a drying tube containing calcium sulfate was added 35 mLs of methylene chloride. The reaction solvent was cooled with an ice water bath. To the flask was added 2.8 grams (0.035 mole) of liquid sulfur trioxide. Thereupon the reaction solution became a very pale clear yellow liquid. The ice water bath cooled reaction vessel was then charged with 5.48 grams (0.035 mole) of phenyl chloroformate added dropwise so as to control the reaction exotherm. When approximately half of the chloroformate had been added, a white precipitate began to form. Upon completion of the addition, the reaction mixture was allowed to warm to room temperature. After six hours at room temperature, a 95%+ conversion was noted by proton nmr analysis. Solvent was removed under vacuum and the remaining white to slightly off-white crystalline solid was used as is for the condensation reaction. The following spectroscopic data was obtained for this material:

Workup

  1. customTo a 100 mL 3-necked round bottom flask equipped with a magnetic stirrer, addition funnel
  2. customtopped with a drying tube
  3. temperatureThe reaction solvent was cooled with an ice water bath
  4. customreaction vessel
  5. additionadded dropwise so as
  6. customthe reaction exotherm
  7. customto form
  8. additionUpon completion of the addition
  9. customSolvent was removed under vacuum
  10. customas is for the condensation reaction
  11. customThe following spectroscopic data was obtained for this material

Sources & evidence

ORD record
ord-91b7b09917cf4a8cb7db79cea94531d2
Source dataset
uspto-grants-1991_01
Patent number
US04985561

Reaction notes

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