Water → 2-(Pyridin-3-ylmethylthio)benzoic acid

HRID 252214Notes

Reaction equation

HRID 252214 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][S:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([O:13]C)=[O:12])[CH:2]=1.[Li+].[OH-].O>CO.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][S:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([OH:13])=[O:12])[CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 58924355Methyl 2-(pyridin-3-ylmethylthio)benzoate

Product 1

HCID 167904922-(Pyridin-3-ylmethylthio)benzoic acidYield 67.3%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of compound 3 (55.0 g, 0.212 mol) in MeOH/H2O (300 mL/50 mL) was added LiOH. H2O (17.8 g, 0.425 mol) in portions at 0° C. The reaction mixture was stirred at room temperature overnight and TLC showed the starting material was consumed. The solvent was removed under reduced pressure. The residue was diluted with water, and extracted with Et2O (2×1 L) to remove neutral impurities. The aqueous layer was adjusted to pH 3-4 with 1 N aq. HCl (50 mL) and extracted with EtOAc (2×1 L). The combined organic phases were washed with water (2×200 mL), brine (300 mL), dried over Na2SO4 and concentrated to afford compound 4 (35.0 g, 67%). This was used without further purification.

Workup

  1. customat 0° C
  2. customwas consumed
  3. customThe solvent was removed under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionextracted with Et2O (2×1 L)
  6. customto remove neutral impurities
  7. extractionextracted with EtOAc (2×1 L)
  8. washThe combined organic phases were washed with water (2×200 mL), brine (300 mL)
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-5ce0f649baee4beab95dd8c653e99807
Source dataset
uspto-grants-2011_01
Patent number
US07868026B2

Reaction notes

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