Hydrochloric Acid → 2-(2-(3-((Quinolin-2-yl)methyloxy)phenoxymethyl)phenoxy)propionic acid

HRID 2073900Notes

Reaction equation

HRID 2073900 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:32]=[CH:33][CH:34]=1)[O:16][CH2:17][C:18]1[CH:31]=[CH:30][CH:29]=[CH:28][C:19]=1[O:20][CH:21]([CH3:27])[C:22]([O:24]CC)=[O:23].[OH-].[Na+].Cl>CCO>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:32]=[CH:33][CH:34]=1)[O:16][CH2:17][C:18]1[CH:31]=[CH:30][CH:29]=[CH:28][C:19]=1[O:20][CH:21]([CH3:27])[C:22]([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11113252Ethyl 2-(2-(3-((quinolin-2-yl)methyloxy)phenoxymethyl)phenoxy)propionate

Product 1

HCID 147741272-(2-(3-((Quinolin-2-yl)methyloxy)phenoxymethyl)phenoxy)propionic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2.65 mmol) of the ester from step C in 25 ml of EtOH is added 10 ml (10.0 mmol, 3.75 equiv) of 1N NaOH. The mixture is stirred for 1 hour at room temperature which time the mixture is acidified to pH~4 using 1N HCl. A precipitate forms which is filtered off and recrystallized from hot MeOH-Et2O to afford 2-(2-(3-((quinolin-2-yl)methyloxy)phenoxymethyl)phenoxy)propionic acid.

Workup

  1. filtrationA precipitate forms which is filtered off
  2. customrecrystallized from hot MeOH-Et2O

Sources & evidence

ORD record
ord-d7e0f0807ff44fb299122ae6caa27b5f
Source dataset
uspto-grants-1990_04
Patent number
US04920131

Reaction notes

Loading…