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

HRID 1023083Notes

Reaction equation

HRID 1023083 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-d6f6a43d3d1144c9b2cb355ddb2d5cf3
Source dataset
uspto-grants-2014_05
Patent number
US08722658B2

Reaction notes

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