Citric Acid → 4-(3-chlorophenyl)sulfonylbenzoic acid

HRID 1911147Notes

Reaction equation

HRID 1911147 reaction equation
C[O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO.O>[Cl:19][C:15]1[CH:14]=[C:13]([S:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:20])=[O:2])=[CH:5][CH:6]=2)(=[O:11])=[O:12])[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 59625905HCID 59625905, compound

Product 1

HCID 3438084-(3-chlorophenyl)sulfonylbenzoic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of compound 31a (138 mg, 0.44 mmol) and LiOH (42 mg, 1.77 mmol) in THF/MeOH/H2O (2/2/2 mL) was stirred for 4 h. A 15% citric acid solution (10 mL) was added. The mixture was then extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The resultant residue, compound 31b (130 mg) was dried under reduced pressure for 18 h and used without further purification.

Workup

  1. extractionThe mixture was then extracted with EtOAc (3×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dry with materialThe resultant residue, compound 31b (130 mg) was dried under reduced pressure for 18 h
  7. customused without further purification

Sources & evidence

ORD record
ord-188be11f64ef42f3876eee02103414f1
Source dataset
uspto-grants-2013_12
Patent number
US08604017B2

Reaction notes

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