Sodium Hydroxide → 2-(Benzyloxy)-5-(piperidin-1-yl)benzoic acid

HRID 454498Notes

Reaction equation

HRID 454498 reaction equation
[OH-].[Na+].O1CCOCC1.[CH2:9]([O:16][C:17]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:23][C:18]=1[C:19]([O:21]C)=[O:20])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)(=O)C>[CH2:9]([O:16][C:17]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:23][C:18]=1[C:19]([OH:21])=[O:20])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 66990377Methyl 2-(benzyloxy)-5-(piperidin-1-yl)benzoate

Product 1

HCID 669910632-(Benzyloxy)-5-(piperidin-1-yl)benzoic acidYield 89.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 4 mol/L aqueous solution of sodium hydroxide (9.8 mL) was added to a dioxane (45 mL) solution of the obtained methyl 2-(benzyloxy)-5-(piperidin-1-yl)benzoate (4.3 g), followed by stirring at room temperature for 1 hour and then at 50 to 55° C. for 2 hours. After cooling the reaction mixture to room temperature, the reaction mixture was adjusted to a pH of 6.3 with acetic acid, and the solvent was evaporated under reduced pressure. Water was added to the obtained residue, and the solid substance was collected by filtration to obtain 3.7 g of 2-(benzyloxy)-5-(piperidin-1-yl)benzoic acid as a white solid.

Workup

  1. waitat 50 to 55° C. for 2 hours
  2. temperatureAfter cooling the reaction mixture to room temperature
  3. customthe solvent was evaporated under reduced pressure
  4. additionWater was added to the obtained residue
  5. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-492a1f41034a4572a9dc669e8d136dd5
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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