Methanol → 110955-49-2

HRID 1059479Notes

Reaction equation

HRID 1059479 reaction equation
S([O-])([O-])=O.[Na+].[Na+].Cl[S:8]([C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)(=[O:10])=[O:9].C(=O)(O)[O-].[Na+].CO>O>[S:8]([C:11]1[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=1)([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 887MethanolHCID 24437Sodium SulfiteHCID 516892Sodium Bicarbonate2×HCID 4738388Methyl 4-(Chlorosulfonyl)benzoate

Product 1

HCID 3783336110955-49-2Yield 78.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium sulfite (15.3 g, 121.45 mMole), was dissolved in water (100 mL) and while stirring at room temperature, methyl 4-chlorosulfonylbenzoate (3), (19.0 g, 80.97 mMole) was added a little at a time to the solution. Sodium bicarbonate was added simultaneously in small portions keeping the solution at approximately pH 8. As the reaction proceeds, periodic addition of a little methanol from a wash bottle minimizes foaming. A total of 20 g of sodium bicarbonate were needed to complete the reaction. After complete addition of the reagents, the mixture was then stirred at room temperature for about 30 minutes. The mixture was then filtered. The clear solution was acidified with concentrated hydrochloric acid and treated with sufficient solid sodium chloride to precipitate the product. The white solid was filtered off and air-dried to give 12.7 g of methyl 4-sulfinobenzoate.

Workup

  1. customthe reaction
  2. additionAfter complete addition of the reagents
  3. stirringthe mixture was then stirred at room temperature for about 30 minutes
  4. filtrationThe mixture was then filtered
  5. additiontreated with sufficient solid sodium chloride
  6. customto precipitate the product
  7. filtrationThe white solid was filtered off
  8. customair-dried

Sources & evidence

ORD record
ord-89041e1eea0f489b90c57a5c9fb4a83a
Source dataset
uspto-grants-2003_02
Patent number
US06521395B1

Reaction notes

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