Methanesulfonyl chloride → HCID 21707336, compound

HRID 1873104Notes

Reaction equation

HRID 1873104 reaction equation
C([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH2:10])=[CH:7][CH:6]=1)(=O)C.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>C[N+](C)(C)C.[OH-]>[CH3:13][S:14]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH2:10])=[CH:7][CH:6]=1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 758214-Ethenylphenyl acetate

Product 1

HCID 21707336HCID 21707336, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 60966Tetramethylammonium hydroxideSolvent

Conditions

Temperature
5 °C

Procedure

Approximately 100 gs (6.17×10-1 moles) of 4-acetoxystyrene was added slowly to a cooled stirred solution (480 mL) of 25% TMAH (the temperature was maintained below 25° C. during the addition.) After about 1/2 to 1 hour of stirring, a clear, yellowish solution was obtained. This solution was cooled to 5° C. and the methanesulfonyl chloride 79.5 gs (0.75×10-1 moles) was added with stirring while the temperature was kept below 15° C through cooling with an ice bath. The reaction mixture was stirred for 1/2 hour until neutral pH was observed in the solution. After this time the resulting crystals were filtered-off, washed with distilled water, and sucked dry. The crystals were dissolved in a minimal amount of methylene chloride and recrystallized by addition of hexane. In this way 76 gs (62% yield) of white crystals were recovered. Analysis of the product indicated:

Workup

  1. temperaturewas maintained below 25° C. during the addition
  2. customa clear, yellowish solution was obtained
  3. stirringwith stirring while the temperature
  4. customwas kept below 15° C
  5. temperaturethrough cooling with an ice bath
  6. stirringThe reaction mixture was stirred for 1/2 hour until neutral pH
  7. washwashed with distilled water
  8. customsucked dry
  9. dissolutionThe crystals were dissolved in a minimal amount of methylene chloride
  10. customrecrystallized by addition of hexane

Sources & evidence

ORD record
ord-b1b65707509b437f946b4e17423c5438
Source dataset
uspto-grants-2000_08
Patent number
US06111133

Reaction notes

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