Sodium Hydroxide → alpha-Oxo-4-[4-(3-pyridinyl)butoxy]benzeneacetic acid

HRID 2225724Notes

Reaction equation

HRID 2225724 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:17]=[N:18][CH:19]=[CH:20][CH:21]=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:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:9][CH:10]=1)[C:3]([OH:23])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53999955alpha-Oxo-4-[4-(3-pyridinyl)butoxy]benzeneacetic acid methyl ester

Product 1

HCID 19004529alpha-Oxo-4-[4-(3-pyridinyl)butoxy]benzeneacetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of alpha-oxo-4-[4-(3-pyridinyl)butoxy]benzeneacetic acid methyl ester (4:1) molar hydrate (1.1 g) in hot methanol (10 mL) was treated with 1N sodium hydroxide (5 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 (2.5 mL) was added dropwise and the product was allowed to crystallize and was filtered and air dried. Recrystallization from acetone provided 0.64 g of alpha-oxo-4-[4-(3-pyridinyl)butoxy]benzeneacetic acid as a colorless solid, mp 163°-165° 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 (2.5 mL) was added dropwise
  6. customto crystallize
  7. filtrationwas filtered
  8. customair dried
  9. customRecrystallization from acetone

Sources & evidence

ORD record
ord-f500ed19fdbc4bf8bdb8bcfe42a07957
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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