Lithium Hydroxide → 4-(3-Pyridylmethyloxymethyl)-2-phenylbenzoic acid

HRID 2121158Notes

Reaction equation

HRID 2121158 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:6][C:5]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Li+]>CO>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH2:12][O:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:25])=[O:2])=[C:5]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:6]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 54057376HCID 54057376, compound

Product 1

HCID 234361714-(3-Pyridylmethyloxymethyl)-2-phenylbenzoic acidYield 93.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution in methanol (5 mL) of [4-(3-pyridylmethyloxymethyl)-2-phenylbenzoic acid methyl ester (0.58 g), prepared as in Example 183A, was added saturated aqueous lithium hydroxide and the reaction mixture was stirred overnight at ambient temperature. The reaction mixture was warmed to 60° C. and stirred for 4 hours. The reaction mixture was concentrated in vacuo and the residue was taken up in water. The aqueous phase was taken to pH 5 with aqueous 3N HCl and extracted with chloroform. The organic phase was concentrated in vacuo to give 4-(3-pyridylmethyloxymethyl)-2-phenylbenzoic acid (0.52 g).

Workup

  1. temperatureThe reaction mixture was warmed to 60° C.
  2. stirringstirred for 4 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. extractionextracted with chloroform
  5. concentrationThe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-454e01ac0f8141d5a0214d53f659d1c9
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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