Hydrochloric Acid → 1-Naphthalenesulfinic acid

HRID 465490Notes

Reaction equation

HRID 465490 reaction equation
C(=O)(O)[O-].[Na+].S([O-])([O-])=O.[Na+].[Na+].[C:12]1([S:22](Cl)(=[O:24])=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.Cl>O>[C:12]1([S:22]([OH:24])=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24437Sodium SulfiteHCID 665601-Naphthalenesulfonyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 108887691-Naphthalenesulfinic acidYield 62.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a vigorously stirred solution of sodium bicarbonate (8.4 g, 100 mmol) and anhydrous sodium sulphite (12 g, 95 mmol) in water (50 ml) at 70°-80° C., was added naphthalene-1-sulphonyl chloride (11.5 g, 50 mmol) in portions and with vigorous stirring. The temperature was kept at 70°-80° C. by intermittent heating. When the addition was complete, the mixture was heated and stirred at 70°-80° C. for a further hour. The mixture was then allowed to cool to room temperature over 4 hours and acidified with 2M hydrochloric acid. The precipitated solid was collected by filtration, washed with water, air dried and then recrystallised from aqueous ethanol to give naphthalene-1-sulphinic acid as a solid (6.0 g), m.p. 86 87° C.

Workup

  1. customwas kept at 70°-80° C. by intermittent heating
  2. additionWhen the addition
  3. temperaturethe mixture was heated
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water, air
  6. customdried
  7. customrecrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-06d7c58b39304e26bb5fc049d63eb8c2
Source dataset
uspto-grants-1992_10
Patent number
US05153227

Reaction notes

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