Sulfuric Acid → Benzoic acid, 5-sulfino-2-(trifluoromethoxy)-

HRID 1820723Notes

Reaction equation

HRID 1820723 reaction equation
Cl[S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:14][C:15]([F:18])([F:17])[F:16])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])(=[O:4])=[O:3].S([O-])([O-])=O.[Na+].[Na+].[OH-].[Na+].OS(O)(=O)=O>O>[S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:14][C:15]([F:16])([F:17])[F:18])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])([OH:4])=[O:3]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 86600705845616-29-72×

Product 1

HCID 69037717Benzoic acid, 5-sulfino-2-(trifluoromethoxy)-Yield 99.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-chlorosulfonyl-2-trifluoromethoxy-benzoic acid (1.0 g, compound 2.9.a) was added portionwise onto a solution of sodium sulfite (3.1 g) in 16 mL of water. The reaction mixture was kept under basic conditions by the addition of the proper amount of 20% NaOH and was stirred at room temperature for 45 minutes. After such time the reaction mixture was cooled down with an ice bath and was then acidified by the addition of 20% H2SO4 solution until reaching pH 2. The solution was then extracted several times with diethyl ether and ethyl acetate. The combined organic phases were dried (sodium sulfate) and concentrated in vacuo to yield the title compound as a white solid (0.88 g).

Workup

  1. temperatureAfter such time the reaction mixture was cooled down with an ice bath
  2. extractionThe solution was then extracted several times with diethyl ether and ethyl acetate
  3. dry with materialThe combined organic phases were dried (sodium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-853ace481e8847d4823cc5fb22d16bfb
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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