Sodium Hydroxide → 4-(quinolin-2-ylmethoxy)benzoic Acid

HRID 1090793Notes

Reaction equation

HRID 1090793 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>C(O)C>[N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][C:12]=1[CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:22])=[O:2])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19934817Methyl 4-(2-quinolinylmethoxy)benzoate

Product 1

HCID 98385524-(quinolin-2-ylmethoxy)benzoic AcidYield 65.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.00 g of methyl-4-(quinolin-2-ylmethoxy)benzoate is dissolved in 120 ml of ethanol and 90 ml of 1N sodium hydroxide and the mixture is stirred at room temperature for 4 days. The mixture is concentrated in vacuo to remove the ethanol. The residue is diluted with water, acidified to pH 6 and the resulting solid is filtered off and recrystallized from methanol to give 3.12 g 4-(quinolin-2-ylmethoxy)benzoic acid.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customto remove the ethanol
  3. additionThe residue is diluted with water
  4. filtrationthe resulting solid is filtered off
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-813a8b5498a34ca9a99a75095311e39c
Source dataset
uspto-grants-1992_01
Patent number
US05082849

Reaction notes

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