Hydrochloric Acid → (4-methylphenyl)sulfonyl acetate

HRID 1389965Notes

Reaction equation

HRID 1389965 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[C:14](Cl)(=[O:16])[CH3:15]>>[C:2]1([CH3:12])[CH:3]=[CH:4][C:5]([S:8]([O:11][C:14](=[O:16])[CH3:15])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 292480(4-methylphenyl)sulfonyl acetate

Conditions

Temperature
60 °C

Procedure

Acetyl chloride (100 ml.; density=1.104 g./ml.) was charged into a suitable reaction flask containing 30 g. (0.158 mole) p-toluenesulfonic acid monohydrate. Vigorous evolution of HCl gas occurred immediately. An efficient HCl trap was attached to the reaction system. The reaction mixture was then heated to mild reflux (~55° C.) and was held to this temperature for 25 minutes. Heating was stopped and the reaction mixture allowed to drop to room temperature over 10-20 minutes with stirring. Vacuum (~20-50 mm) was applied cautiously to remove acetyl chloride without carryover. At the same time the mixture was heated gradually to 60° C. Distillation of acetyl chloride was complete in ~30 minutes with collection in an ice cold flask for reuse. The oil obtained was then subjected to vacuum (~5-10 mm) to remove the last traces of acetyl chloride and acetic acid at 37° C. A snow white solid then crystallized in about 30 minutes as the title product.

Workup

  1. additioncontaining 30 g
  2. customAn efficient HCl trap was attached to the reaction system
  3. temperatureThe reaction mixture was then heated
  4. temperatureto mild reflux (~55° C.)
  5. temperatureHeating
  6. waitto drop to room temperature over 10-20 minutes
  7. customto remove acetyl chloride without carryover
  8. distillationDistillation of acetyl chloride
  9. customwas complete in ~30 minutes with collection in an ice cold flask for reuse
  10. customThe oil obtained
  11. customto remove the last traces of acetyl chloride and acetic acid at 37° C
  12. customA snow white solid then crystallized in about 30 minutes as the title product

Sources & evidence

ORD record
ord-28c9b638db4f462a9494ae3d17617c2a
Source dataset
uspto-grants-1981_01
Patent number
US04247461

Reaction notes

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