Lithium Hydroxide → 2-(4-(1-(((4-(Trifluoromethyl)benzyl)oxy)imino)propyl)phenoxy)acetic acid

HRID 68308Notes

Reaction equation

HRID 68308 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:27]=[CH:26][C:6]([CH2:7][O:8][N:9]=[C:10]([C:13]2[CH:25]=[CH:24][C:16]([O:17][CH2:18][C:19]([O:21]CC)=[O:20])=[CH:15][CH:14]=2)[CH2:11][CH3:12])=[CH:5][CH:4]=1.[OH-].[Li+]>C1COCC1.O>[F:1][C:2]([F:28])([F:29])[C:3]1[CH:27]=[CH:26][C:6]([CH2:7][O:8][N:9]=[C:10]([C:13]2[CH:14]=[CH:15][C:16]([O:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:24][CH:25]=2)[CH2:11][CH3:12])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 74371516Ethyl 2-(4-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)propyl)phenoxy)acetate

Product 1

HCID 743706342-(4-(1-(((4-(Trifluoromethyl)benzyl)oxy)imino)propyl)phenoxy)acetic acidYield 88.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of the product of step 3 (28 g, 0.0683 moles) in THF (140 ml), a solution of lithium hydroxide (4.3 g, 0.1024 moles) in water (140 ml) was added and the reaction mixture was stirred at 25° C. for 3 hours. The solvents were evaporated under reduced pressure. The residue was dissolved in water, acidified with 1N HCl and extracted with ethyl acetate. The combined ethyl acetate extract was washed with water & brine, dried over sodium sulphate and evapourated under reduced pressure to yield 23 gm (88%) of product as solid.

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with ethyl acetate
  4. extractionThe combined ethyl acetate extract
  5. washwas washed with water & brine
  6. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-eb710248ab6c4f938a4f3cbc762656e6
Source dataset
uspto-grants-2014_09
Patent number
US08822414B2

Reaction notes

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