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

HRID 454466Notes

Reaction equation

HRID 454466 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)=[CH:23][C:12]=1[C:13]([O:15]CC1C=CC=CC=1)=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCOCC1.CO>[CH2:3]([O:10][C:11]1[CH:26]=[CH:25][C:24]([C:27]2[CH:28]=[CH:29][N:30]=[CH:31][CH:32]=2)=[CH:23][C:12]=1[C:13]([OH:15])=[O:14])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66990917Benzyl 2-(benzyloxy)-5-(pyridin-4-yl)benzoate

Product 1

HCID 669904822-(Benzyloxy)-5-(pyridin-4-yl)benzoic acidYield 84.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

An 2 mol/L aqueous solution of sodium hydroxide (1.1 mL) was added to a solution mixture of the obtained benzyl 2-(benzyloxy)-5-(pyridin-4-yl)benzoate (0.29 g) in dioxane (2.9 mL) and methanol (2.9 mL), followed by stirring at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and water was added to the residue. After adjusting the pH to 4 with 6 mol/L hydrochloric acid, ethyl acetate was added thereto. The reaction mixture was filtrated to collect the solid substance to obtain 0.19 g of 2-(benzyloxy)-5-(pyridin-4-yl)benzoic acid as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and water
  2. additionwas added to the residue
  3. additionwas added
  4. filtrationThe reaction mixture was filtrated
  5. customto collect the solid substance

Sources & evidence

ORD record
ord-da2df13d770f4f00851db2034ce6556e
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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