Citric Acid → 4-[(3-Chlorophenyl)thio]benzoic acid

HRID 1911146Notes

Reaction equation

HRID 1911146 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([S:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 59625879HCID 59625879, compound

Product 1

HCID 157278294-[(3-Chlorophenyl)thio]benzoic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of compound 30c (320 mg, 1.15 mmol), LiOH (110 mg, 4.59 mmol) in THF/MeOH/H2O (3/3/3 mL) was stirred for 4 h. A 15% aqueous citric acid solution (10 mL) was added. The mixture was then extracted with EtOAc (3×). The combined organic extracts were washed with brine, filtered, dried over Na2SO4, and concentrated under reduced pressure. The resultant residue (compound 30d, 290 mg) was dried under reduced pressure for 18 h and was used without further purification.

Workup

  1. extractionThe mixture was then extracted with EtOAc (3×)
  2. washThe combined organic extracts were washed with brine
  3. filtrationfiltered
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. dry with materialThe resultant residue (compound 30d, 290 mg) was dried under reduced pressure for 18 h
  7. customwas used without further purification

Sources & evidence

ORD record
ord-dd7293ca75eb4373aaebdc59a0d20db3
Source dataset
uspto-grants-2013_12
Patent number
US08604017B2

Reaction notes

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