Potassium Hydroxide → (4-Pyridin-2-YL-phenyl)-acetic acid

HRID 2213529Notes

Reaction equation

HRID 2213529 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([O:16]C)=[O:15])=[CH:9][CH:8]=1.[OH-].[K+]>O1CCCC1.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 12094242Methyl 2-(4-(pyridin-2-yl)phenyl)acetate

Product 1

HCID 504301(4-Pyridin-2-YL-phenyl)-acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

700 mg (3.11 mol) of methyl [4-(2-pyridinyl)phenyl]acetate are initially charged in 5 ml of tetrahydrofuran and, at room temperature, admixed with 6.2 ml of a 1M potassium hydroxide solution in water. The mixture is then stirred at room temperature for 18 h, most of the solvent is removed under reduced pressure and the residue is taken up in 10 ml of water and adjusted to a pH of about 5 using 2N hydrochloric acid. The aqueous phase was extracted twice, in each case with 10 ml of dichloromethane, the combined organic phases were dried over magnesium sulphate and the solvent was removed under reduced pressure, giving the compound of Example VIII in the form of a solid.

Workup

  1. customis removed under reduced pressure
  2. extractionThe aqueous phase was extracted twice, in each case with 10 ml of dichloromethane
  3. dry with materialthe combined organic phases were dried over magnesium sulphate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-23fd563ab03e40bdbdddc196e35192e5
Source dataset
uspto-grants-2006_09
Patent number
US07105553B2

Reaction notes

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