Sodium Hydroxide → 4-(3-Pyridyloxymethyl)2-phenylbenzoic acid

HRID 2121196Notes

Reaction equation

HRID 2121196 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:6][C:5]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[Na+]>CO>[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:24])=[O:2])=[C:5]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:6]=2)[CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 106870984-(3-Pyridyloxymethyl)2-phenylbenzoic acid methyl ester

Product 1

HCID 234363704-(3-Pyridyloxymethyl)2-phenylbenzoic acidYield 98.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(3-pyridyloxymethyl)-2-phenylbenzoic acid methyl ester (3.4 g, 10.6 mmol), prepared as in Example 228C, in methanol (30 mL) was added aqueous 4N sodium hydroxide and the reaction mixture was heated at reflux for 6 hours. The methanol was distilled of in vacuo and the residue was taken up in water. The aqueous solution was taken to pH 4 with HCl and the resulting precipitate was filtered off and dried to give 4-(3-pyridyloxymethyl)-2-phenylbenzoic acid (3.2 g).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 6 hours
  3. distillationThe methanol was distilled of in vacuo
  4. filtrationthe resulting precipitate was filtered off
  5. customdried

Sources & evidence

ORD record
ord-399e1713051a4d159e4a34148ef4e8cf
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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