Sulfuric Acid → 4-Ethylbenzene-1-sulfonyl chloride

HRID 2352066Notes

Reaction equation

HRID 2352066 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:7].[S:14](=[O:18])(=O)(O)[OH:15]>O>[CH2:6]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([Cl:3])(=[O:18])=[O:15])=[CH:10][CH:9]=1)[CH3:7]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7500EthylbenzeneHCID 24813Phosphorus oxychloride

Product 1

HCID 5709594-Ethylbenzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
69 °C

Procedure

With stirring, 929.0 g phosphorus oxychloride was added to 836.0 g ethylbenzene. The resulting mixture was heated to approximately 69° C. and 599.0 g of 100 percent sulfuric acid was added over approximately sixteen minutes with the temperature rising to approximately 78° C. and it continued to slowly rise over approximately thirty-seven minutes to approximately 84° C. The mixture was held at approximately 80° C. for about two hours and then maintained at approximately 90° C. for an additional three hours. After cooling to approximately 82° C. the reaction mixture was poured slowly onto a mixture of 1500.0 ml water and 1500.0 g ice keeping the temperature under 5° C. with the addition of 440.0 g ice. After approximately ten minutes of stirring, the agitation was stopped and the mixture separated into two layers. The lower layer containing the product was separated and immediately poured onto 500.0 g of ice and 3500.0 ml of ice water was added. After approximately twenty minutes of stirring, the layers were separated to obtain 1400.0 ml of 4-ethylbenzenesulfonyl chloride.

Workup

  1. customrising to approximately 78° C.
  2. temperaturemaintained at approximately 90° C. for an additional three hours
  3. temperatureAfter cooling to approximately 82° C. the reaction mixture
  4. stirringAfter approximately ten minutes of stirring
  5. customthe mixture separated into two layers
  6. additionThe lower layer containing the product
  7. customwas separated
  8. additionimmediately poured onto 500.0 g of ice and 3500.0 ml of ice water
  9. additionwas added
  10. stirringAfter approximately twenty minutes of stirring
  11. customthe layers were separated

Sources & evidence

ORD record
ord-9750cd94703343c2af47369c82e27513
Source dataset
uspto-grants-1989_10
Patent number
US04874894

Reaction notes

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