Sodium Hydroxide → {o-{5-[(2-Chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl)oxy]-2-nitrophenoxy}phenoxy}acetic acid

HRID 21522Notes

Reaction equation

HRID 21522 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:12]=[CH:13][C:14]([N+:30]([O-:32])=[O:31])=[C:15]([CH:29]=2)[O:16][C:17]2[CH:28]=[CH:27][CH:26]=[CH:25][C:18]=2[O:19][CH2:20][C:21]([O:23]C)=[O:22])[CH:7]=[C:6]([F:33])[C:5]=1[C:34]([F:37])([F:36])[F:35]>CO>[Cl:3][C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:12]=[CH:13][C:14]([N+:30]([O-:32])=[O:31])=[C:15]([CH:29]=2)[O:16][C:17]2[CH:28]=[CH:27][CH:26]=[CH:25][C:18]=2[O:19][CH2:20][C:21]([OH:23])=[O:22])[CH:7]=[C:6]([F:33])[C:5]=1[C:34]([F:37])([F:35])[F:36]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86748719Methyl {o-{5-[(2-chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl)oxy]-2-nitrophenoxy}phenoxy}acetate

Product 1

HCID 86748718{o-{5-[(2-Chloro-alpha,alpha,alpha,6-tetrafluoro-p-tolyl)oxy]-2-nitrophenoxy}phenoxy}acetic acidYield 39.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroxide solution (10 mL of a one normal solution, 0.01 mol) is added to a solution of methyl {o-{5-[(2-chloro-α,α,α,6-tetrafluoro-p-tolyl)oxy]-2-nitrophenoxy}phenoxy}acetate (5.25 g, 0.01 mol) in methanol. The reaction mixture is stirred for three hours, concentrated in vacuo and dissolved in water. The aqueous solution is adjusted to pH 3 with 2.5N hydrochloric acid and extracted with methylene chloride. The organic extract is washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain the title product as a white solid (2 g) which is identified by 1HNMR and 13CNMR spectral analyses.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutiondissolved in water
  3. extractionextracted with methylene chloride
  4. extractionThe organic extract
  5. washis washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-687da6d273c64f0b9c1b8cba3b5ec032
Source dataset
uspto-grants-1995_06
Patent number
US05424280

Reaction notes

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