Sodium Hydroxide → 3-(4-Methoxyphenoxy)benzoic acid

HRID 1681549Notes

Reaction equation

HRID 1681549 reaction equation
[OH-:1].[Na+].[CH3:3][O:4][C:5]1[CH:19]=[CH:18][C:8]([O:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[CH:13]=[O:14])=[CH:7][CH:6]=1>O.[Ag]=O>[CH3:3][O:4][C:5]1[CH:19]=[CH:18][C:8]([O:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]([OH:1])=[O:14])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 1235533-(4-Methoxyphenoxy)benzaldehyde

Product 1

HCID 6185083-(4-Methoxyphenoxy)benzoic acidYield 61.7%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 962WaterSolvent

Procedure

To a suspension of 10.6 g of silver oxide in 75 ml of water were added 7 g of sodium hydroxide. Ten grams of 3-(4-methoxyphenoxy)benzaldehyde were added in dropwise fashion and the reaction mixture was heated to 60°-70° C. for one hour. The mixture was filtered, the filtrate was acidified to pH 2 with hydrochloric acid, and the resulting precipitate was recovered by filtration. Crystallization from ethanol/water afforded 6.6 g of the desired subtitle intermediate, m.p. 141°-143° C.

Workup

  1. temperaturethe reaction mixture was heated to 60°-70° C. for one hour
  2. filtrationThe mixture was filtered
  3. filtrationthe resulting precipitate was recovered by filtration
  4. customCrystallization from ethanol/water

Sources & evidence

ORD record
ord-d054353f8ef1425d948d40e1a47860e8
Source dataset
uspto-grants-1992_12
Patent number
US05171882

Reaction notes

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