Sodium Hydroxide → alpha-Oxo-4-[4-(4-pyridinyl)butoxy]benzeneacetic acid

HRID 2225726Notes

Reaction equation

HRID 2225726 reaction equation
C[O:2][C:3](=[O:23])[C:4](=[O:22])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[CH:7][CH:6]=1.[OH-].[Na+]>CO.O>[O:22]=[C:4]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[CH:9][CH:10]=1)[C:3]([OH:23])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54486867alpha-Oxo-4-[4-(4-pyridinyl)butoxy]benzeneacetic acid methyl ester

Product 1

HCID 19004403alpha-Oxo-4-[4-(4-pyridinyl)butoxy]benzeneacetic acidYield 99.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of alpha-oxo-4-[4-(4-pyridinyl)butoxy]benzeneacetic acid methyl ester (0.58 g) in hot methanol (10 mL) was treated with 1N sodium hydroxide (3.0 mL) and diluted with water. The organic solvent was removed under vacuum and the residue in water was washed with diethyl ether. The aqueous layer was concentrated to about 25 mL and chilled in ice. Cold 2N hydrochloric acid (1.5 mL) was added dropwise and the product was allowed to crystallize and was filtered and air dried. Recrystallization from water provided 0.55 g of alpha-oxo-4-[4-(4-pyridinyl)butoxy]benzeneacetic acid as a colorless solid, mp 198°-199° C.

Workup

  1. customThe organic solvent was removed under vacuum
  2. washthe residue in water was washed with diethyl ether
  3. concentrationThe aqueous layer was concentrated to about 25 mL
  4. temperaturechilled in ice
  5. additionCold 2N hydrochloric acid (1.5 mL) was added dropwise
  6. customto crystallize
  7. filtrationwas filtered
  8. customair dried
  9. customRecrystallization from water

Sources & evidence

ORD record
ord-51b1c0b45d4a43d1a354e4da7ef85d8b
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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