Sodium Hydroxide → 2-(2-Aminophenoxy)benzoic acid

HRID 1077977Notes

Reaction equation

HRID 1077977 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9]C)=[O:8].[OH-].[Na+]>CO.O>[NH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 16080835HCID 16080835, compound

Product 1

HCID 214610602-(2-Aminophenoxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of Methyl 2-(2-aminophenoxy)benzoate (9.2 g, 0.038 mol) and sodium hydroxide (3.2 g, 0.08 mol) in 1:1 methanol/water (200 mL) was stirred under argon at room temperature for 3 h. The methanol was evaporated, the aqueous residue was acidified with dilute HCl, extracted with ethyl acetate, dried over anhydrous MgSO4, filtered, and evaporated to give the crude product which was purified by flash chromatography (silica gel, ethyl acetate/hexane/formic acid), and then recrystallized from ethyl acetate/hexane to give the title compound as a white crystalline solid; mp 150°-151° C.

Workup

  1. customThe methanol was evaporated
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give the crude product which
  7. customwas purified by flash chromatography (silica gel, ethyl acetate/hexane/formic acid)
  8. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-925c8c3f2ddd42c691e12134fefa79fc
Source dataset
uspto-grants-1996_08
Patent number
US05545669

Reaction notes

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