Lithium Hydroxide → 2-(Benzyloxy)-5-(pyridin-4-yl)benzoic acid

HRID 1623700Notes

Reaction equation

HRID 1623700 reaction equation
[Li+].[OH-].[C:3]1([CH2:9][O:10][C:11]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)=[CH:23][C:12]=2[C:13]([O:15]CC2C=CC=CC=2)=[O:14])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCCC1.O>[C:3]1([CH2:9][O:10][C:11]2[CH:26]=[CH:25][C:24]([C:27]3[CH:28]=[CH:29][N:30]=[CH:31][CH:32]=3)=[CH:23][C:12]=2[C:13]([OH:15])=[O:14])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66990917Benzyl 2-(benzyloxy)-5-(pyridin-4-yl)benzoate

Product 1

HCID 669904822-(Benzyloxy)-5-(pyridin-4-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Solid LiOH (0.79 g, 18.77 mmol) was added to a stirred solution of phenylmethyl 2-[(phenylmethyl)oxy]-5-(4-pyridinyl)benzoate (may be prepared as described in Description 78; 0.81 g, 1.88 mmol) in tetrahydrofuran (50 ml) and water (10 ml) in air at room temperature. The reaction mixture was stirred at 70° C. overnight. After the reaction mixture was cooled to room temperature, the solvent was removed and the residue was dissolved in water (100 ml) and stirred in an ice-water bath. 1N HCl (aq) was added to adjust the pH to 4. The solid was filtered, and dissolved in ethyl acetate (80 ml). The solution was dried over Na2SO4, filtered, and concentrated under reduced pressure to yield the title compound as a white solid, 486 mg.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customthe solvent was removed
  3. dissolutionthe residue was dissolved in water (100 ml)
  4. stirringstirred in an ice-water bath
  5. addition1N HCl (aq) was added
  6. filtrationThe solid was filtered
  7. dissolutiondissolved in ethyl acetate (80 ml)
  8. dry with materialThe solution was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fdc2c724d0c74639be7264bc26f17f5b
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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