Citric Acid → 4-((5-Chloropyridin-3-yl)methoxy)benzoic acid

HRID 401658Notes

Reaction equation

HRID 401658 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=2)[CH:5]=[N:6][CH:7]=1.[Li+].[OH-].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=2)[CH:5]=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 59625946Methyl 4-((5-chloropyridin-3-yl)methoxy)benzoate

Product 1

HCID 596257314-((5-Chloropyridin-3-yl)methoxy)benzoic acidYield 89.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 27b (1.22 mmol, 340 mg) was combined with LiOH (4.9 mmol, 118 mg) in 3 mL of THF, 3 mL of MeOH, and 3 mL of water. The mixture was stirred at room temperature for 4 h and was then combined with 15% aqueous citric acid and extracted with EtOAc. The extracts were washed with water and brine, dried over Na2SO4, and concentrated under vacuum to give 288 mg of 27c.

Workup

  1. extractionextracted with EtOAc
  2. washThe extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f7d36b19476b41248bcd086b4b27209a
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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