Methyl 3-isopropoxy-5-(3-pyridin-3-ylpropoxy)benzoate → 3-Isopropoxy-5-(3-pyridin-3-ylpropoxy)benzoic acid

HRID 1644584Notes

Reaction equation

HRID 1644584 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([O:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:14]=1)[C:8]([O:10]C)=[O:9])([CH3:3])[CH3:2]>C1COCC1.CO.[OH-].[Na+]>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([O:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:14]=1)[C:8]([OH:10])=[O:9])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 66775698Methyl 3-isopropoxy-5-(3-pyridin-3-ylpropoxy)benzoate

Product 1

HCID 592430633-Isopropoxy-5-(3-pyridin-3-ylpropoxy)benzoic acidYield 60%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 3-isopropoxy-5-(3-pyridin-3-ylpropoxy)benzoate (2.70 g) was dissolved in a mixed solvent of THF (30 ml) and methanol (30 ml), and 1N aqueous sodium hydroxide solution (25 ml) was added to the mixed solution. The mixture was stirred overnight at room temperature and concentrated under reduced pressure to dryness. 1N Aqueous hydrochloric acid solution (25 ml) was added thereto, and the precipitated crystals were collected by filtration and washed with water to give 3-isopropoxy-5-(3-pyridin-3-ylpropoxy)benzoic acid (1.55 g, 60%) as colorless crystals.

Workup

  1. additionwas added to the mixed solution
  2. concentrationconcentrated under reduced pressure to dryness
  3. addition1N Aqueous hydrochloric acid solution (25 ml) was added
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-41d24c51cc214bbd9ccdddf2cfe23458
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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