Hydrochloric Acid → 2-(Benzyloxy)-4-(pyridin-3-yl)benzoic acid

HRID 454464Notes

Reaction equation

HRID 454464 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:26]=[C:25]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[CH:24]=[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.O.Cl>O1CCOCC1.CO.C(OCC)(=O)C>[CH2:3]([O:10][C:11]1[CH:26]=[C:25]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[CH:24]=[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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 66990951Benzyl 2-(benzyloxy)-4-(pyridin-3-yl)benzoate

Product 1

HCID 669899782-(Benzyloxy)-4-(pyridin-3-yl)benzoic acidYield 74%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A 2 mol/L aqueous solution of sodium hydroxide (1.3 mL) was added to a solution mixture of the obtained benzyl 2-(benzyloxy)-4-(pyridin-3-yl)benzoate (0.35 g) in dioxane (1.8 mL) and methanol (1.8 mL), followed by stirring at room temperature for 1 hour. Water was added to the reaction mixture. After adjusting the pH to 4.5 with 6 mol/L hydrochloric acid, ethyl acetate was added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue, and the solid substance was collected by filtration to obtain 0.20 g of 2-(benzyloxy)-4-(pyridin-3-yl)benzoic acid as a light yellow solid.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. additionDiisopropyl ether was added to the obtained residue
  7. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-cb8f4464a53e4d48a87cd1413f40c64b
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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