Sodium Hydroxide → 2-(2-Pyridyl)-2-(carboxymethoxyphenoxy)-acetic acid

HRID 267789Notes

Reaction equation

HRID 267789 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7].[OH-].[Na+].Br[CH:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)[C:17]([OH:19])=[O:18]>>[N:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH:16]([O:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7])[C:17]([OH:19])=[O:18]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 22783(o-Hydroxyphenoxy)acetic acidHCID 22902942Bromo(pyridin-2-yl)acetic acid

Product 1

HCID 215539422-(2-Pyridyl)-2-(carboxymethoxyphenoxy)-acetic acid

Procedure

A mixture of 2-hydroxyphenoxy acetic acid (16.8 g. 0.1 mole) and 80 ml. of 5N aqueous sodium hydroxide (0.4 mole) is stirred until solution is effected, then the solution treated with 2-bromo-2-(2-pyridyl)-acetic acid (21.6 g. 0.1 mole), and refluxed for 20 hours. The cooled solution is taken to neutrality and the diacid crystallized from benzene to give 2-(2-pyridyl)-2-(carboxymethoxyphenoxy)-acetic acid.

Workup

  1. temperaturerefluxed for 20 hours
  2. customthe diacid crystallized from benzene

Sources & evidence

ORD record
ord-6a1f4f9269c54cb98025609b5bc217a7
Source dataset
uspto-grants-1976_03
Patent number
US03944560

Reaction notes

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