Lithium Hydroxide → 4-[3-(Pyridin-4-yl)propyloxy]benzoic acid

HRID 265884

Reaction equation

HRID 265884 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[CH:13][CH:12]=2)=[CH:3][CH:2]=1.[Li+].[OH-].C1COCC1>C(Cl)Cl.CO.CC(O)=O>[N:1]1[CH:2]=[CH:3][C:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[CH:19][CH:20]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 53832197Methyl 4-[3-(4-pyridinyl)propoxy]benzoate

Product 1

HCID 190341454-[3-(Pyridin-4-yl)propyloxy]benzoic acid

Reagents, catalysts & solvents 1

HCID 21877243DCM MeOH AcOHSolvent

Procedure

A solution of 19-4 (3.2 g, 11.9 mmol), 1N LiOH (25 mL), and THF (50 mL) was stirred overnight at ambient temperature. After 20 h, the solution was washed with EtOAc and then acidified with 10% KHSO4 to give a suspension of white solid. The aqueous portion was extracted with CHCl3 and then the aqueous portion containing the solid was filtered. After drying the solid at 50° C. for 3 h, 19-5 was obtained. Rf 0.47 (silica, 10/1/1 CH2Cl2 /CH3OH/AcOH).

Workup

  1. washthe solution was washed with EtOAc
  2. customto give
  3. additiona suspension of white solid
  4. extractionThe aqueous portion was extracted with CHCl3
  5. additionthe aqueous portion containing the solid
  6. filtrationwas filtered
  7. customAfter drying the solid at 50° C. for 3 h
  8. custom19-5 was obtained

Sources & evidence

ORD record
ord-d4fc639ea6b44fd5b7b8b593e7e817de
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Linked notes

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