Lithium hydroxide, monohydrate → 4-(6-Chloropyridin-3-yl)benzoic acid

HRID 2085755Notes

Reaction equation

HRID 2085755 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.O[Li].O>C1COCC1.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22730372Methyl 4-(6-chloropyridin-3-yl)benzoate

Product 1

HCID 227308064-(6-Chloropyridin-3-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 252F (1.56 g, 6.4 mmol) in THF (30 mL) at room temperature treated with a solution of LiOH.H2O (0.537 g, 12.8 mmol) in water (5 mL), heated to reflux for 4 hours, cooled to room temperature and concentrated. The mixture was neutralized with 1N HCl and extracted ethyl acetate (3×50 mL). The combined extracts were washed with brine, dried (Na2SO4), filtered, and concentrated to provide the desired product. MS (APCI) m/e 234 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. concentrationconcentrated
  4. extractionextracted ethyl acetate (3×50 mL)
  5. washThe combined extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5c4d7ceba39d47199d0143f5de0df654
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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