Potassium Hydroxide → HCID 23436107, compound

HRID 2121144Notes

Reaction equation

HRID 2121144 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7](=[CH:10][O:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH2:6][C:5]=1[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[K+]>CO.O>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:25])=[O:2])=[C:5]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:6]=2)[CH:13]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 69892868HCID 69892868, compound

Product 1

HCID 23436107HCID 23436107, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution in methanol (15 mL) of 4-(3-pyridyloxymethylene)-2-phenoxybenzoic acid methyl ester (2.46 g), prepared as in Example 157E, was added a solution of 5% aqeuous KOH (2.00 g) in water (3 mL). The reaction mixture was heated at reflux for 1.5 hours. The reaction mixture was concentrated in vacuo and the residue was dissolved in water. The aqueous phase was acidified with acetic acid with cooling and stirring. The resulting solid was filtered, washed with water, and dissolved in THF. The THF solution was dried over Na2SO4, filtered, and concentrated in vacuo to give 4-(3-pyridyloxymethyl)-2-phenoxybenzoic acid (2.17 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1.5 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionthe residue was dissolved in water
  5. temperaturewith cooling
  6. filtrationThe resulting solid was filtered
  7. washwashed with water
  8. dissolutiondissolved in THF
  9. dry with materialThe THF solution was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-961172d9fe694e87a1ed713c99a689c9
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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