Lithium hydroxide, monohydrate → 2-(3-(Pyridin-2-yl)phenyl)acetic acid

HRID 1058573Notes

Reaction equation

HRID 1058573 reaction equation
C[O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:6]=1.O[Li].O>C1COCC1.O>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:17])=[O:2])[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 543647723-(2-Pyridyl)-phenyl acetic acid methyl ester

Product 1

HCID 120760552-(3-(Pyridin-2-yl)phenyl)acetic acidYield 106.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound of 3-(2-pyridyl)-phenyl acetic acid methyl ester (3.8 g, 16.7 mmol) in THF (50 mL) was added a solution of LiOH.H2O (780.2 mg, 18.6 mmol) in H2O (10 mL). The reaction was stirred at room temperature until TLC analysis indicated the complete consumption of starting material (2 h). The reaction mixture was concentrated to remove THF, then neutralized to pH=7 by the addition of IN HCl, diluted with brine (50 mL), and washed with CHCl3 (100 mL) The aqueous layer was readjusted back to pH=7 by the addition on IN NaOH and washed with fresh CHCl3 (100 mL). After repeating this procedure once more, the organic layers were combined, dried, filtered (MgSO4) and concentrated to give 3.79 g of the title compound: MS (ES+) 214.3 (MH+).

Workup

  1. customthe complete consumption of starting material (2 h)
  2. concentrationThe reaction mixture was concentrated
  3. customto remove THF
  4. additionneutralized to pH=7 by the addition of IN HCl
  5. additiondiluted with brine (50 mL)
  6. washwashed with CHCl3 (100 mL) The aqueous layer
  7. additionwas readjusted back to pH=7 by the addition on IN NaOH
  8. washwashed with fresh CHCl3 (100 mL)
  9. customdried
  10. filtrationfiltered (MgSO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-ecfd12dceb9446ba9a585d64b6072919
Source dataset
uspto-grants-2003_02
Patent number
US06518267B1

Reaction notes

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