Sodium Hydroxide → 3-Chloro-4-methylbenzenesulfinic acid

HRID 1384502Notes

Reaction equation

HRID 1384502 reaction equation
S([O-])([O-])=O.[Na+].[Na+].[Cl:7][C:8]1[CH:13]=[C:12]([S:14](Cl)(=[O:16])=[O:15])[CH:11]=[CH:10][C:9]=1[CH3:18].[OH-].[Na+]>O>[CH3:18][C:9]1[CH:10]=[CH:11][C:12]([S:14]([OH:16])=[O:15])=[CH:13][C:8]=1[Cl:7]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 2597442-Chloro-p-toluenesulfochloride

Product 1

HCID 27576613-Chloro-4-methylbenzenesulfinic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
52.5 °C

Procedure

2350 ml of water and 420 g (3.3 mol) of sodium sulfite (=15.1% strength Na2SO3 solution) are introduced into a stirrer apparatus equipped with 2 dropping funnels and a pH electrode, and the mixture is heated to 50-55° C. In the course of about 2 h, 677 g (3 mol) of 2-chloro-p-toluenesulfonyl chloride are run in and simultaneously 690 g of NaOH (35% strength) are added dropwise so that a pH of 8-10 is maintained. The temperature is allowed to rise to 65° C. The reaction is completed when the pH remains constant at 8-10. The sodium sulfinate is in solution at 60-65° C., and crystallizes out from about 55° C.

Workup

  1. customequipped with 2 dropping funnels
  2. additionare added dropwise so that a pH of 8-10
  3. temperatureis maintained
  4. customto rise to 65° C
  5. customis in solution at 60-65° C.
  6. customcrystallizes out from about 55° C.

Sources & evidence

ORD record
ord-9e67f8fb0e0d44feb702a833a59eb747
Source dataset
uspto-grants-2001_07
Patent number
US06258984B1

Reaction notes

Loading…