Sodium Sulfite → 4-ethylbenzenesulfinate

HRID 1267830Notes

Reaction equation

HRID 1267830 reaction equation
S([O-])([O-])=O.[Na+:5].[Na+].C(=O)(O)[O-].[Na+].[CH2:12]([C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1)[CH3:13]>O>[CH2:12]([C:14]1[CH:15]=[CH:16][C:17]([S:20]([O-:22])=[O:21])=[CH:18][CH:19]=1)[CH3:13].[Na+:5]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 5709594-Ethylbenzene-1-sulfonyl chloride

Product 1

HCID 36964144-ethylbenzenesulfinateYield 147.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
77.5 °C

Procedure

In a 125 mL, three-necked flask fiited with thermometer, addition funnel, and glass stopper was placed 11.5 grams (91.2 mmol) of sodium sulfite, 8.32 grams (97.7 mmol) of sodium bicarbonate, and 50 mL of water. After heating the mixture to 75-80° C., 10.0 grams (48.9 mmol) of 4-ethylbenzenesulfonyl chloride was added dropwise over 0.5 hours. When the addition was complete, heating was continued for 3 hours at which time a white precipitate formed. The suspension was cooled to room temperature and allowed to stir for 16 hours. The precipitate was collected by filtration, washed with cold water, combined with a second crop from the filtrate, and dried under high vaccum to give 13.9 grams (>100% yield) of crude sodium 4-ethylbenzenesulfinate.

Workup

  1. additionIn a 125 mL, three-necked flask fiited with thermometer, addition funnel, and glass stopper
  2. additionWhen the addition
  3. temperatureheating
  4. customa white precipitate formed
  5. temperatureThe suspension was cooled to room temperature
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with cold water
  8. customdried under high vaccum

Sources & evidence

ORD record
ord-07038ed58e51425192782b7a419eeb6e
Source dataset
uspto-grants-2003_04
Patent number
US06555538B2

Reaction notes

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