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Sodium Hydroxide → {2-[2-Chloro-4-(methylsulfonyl)phenoxy]phenoxy}acetic acid

HRID 1945231
Notes
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Reaction equation

HRID 1945231 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[O:6][CH2:7][C:8]([OH:10])=[O:9].[CH3:15][S:16]([C:19]1[CH:24]=[CH:23][C:22](F)=[C:21]([Cl:26])[CH:20]=1)(=[O:18])=[O:17].[OH-].[Na+]>CN(C=O)C>[Cl:26][C:21]1[CH:20]=[C:19]([S:16]([CH3:15])(=[O:18])=[O:17])[CH:24]=[CH:23][C:22]=1[O:3][C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[O:6][CH2:7][C:8]([OH:10])=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 22783(o-Hydroxyphenoxy)acetic acidHCID 24758Sodium hydrideHCID 213408802-Chloro-1-fluoro-4-methylsulfonylbenzene

Product 1

HCID 58516141{2-[2-Chloro-4-(methylsulfonyl)phenoxy]phenoxy}acetic acid

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
40 °C

Procedure

Sodium hydride (60% disp. oil, 0.24 g) was added to a solution of (2-hydroxyphenoxy)acetic acid (0.5 g) in DMF (20 ml) and stirred at 40° C. for 30 min. The product from example 7 step (ii) (0.62 g) was added, then the mixture heated at 75° C. for 30 h. 2M Sodium hydroxide solution was added and extracted with ethylacetate. The aqueous layer was acidified with 2M hydrochloric acid and extracted with ethyl acetate. The organics were dried, evaporated under reduced pressure and the residue purified by RPHPLC, yield 0.21 g.

Workup

  1. temperaturethe mixture heated at 75° C. for 30 h
  2. extractionextracted with ethylacetate
  3. extractionextracted with ethyl acetate
  4. customThe organics were dried
  5. customevaporated under reduced pressure
  6. customthe residue purified by RPHPLC, yield 0.21 g

Sources & evidence

ORD record
ord-734f0c66a7ce4a178217f2d354d27de8
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08394986B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes