Water → (2E)-2-cyclopentyloxyimino-2-(3,4-dichlorophenyl)acetic acid

HRID 600971Notes

Reaction equation

HRID 600971 reaction equation
C([O:3][C:4](=[O:21])/[C:5](=[N:14]/[O:15][CH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)/[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1)C.[OH-].[Li+].O>C(O)C.C(Cl)(Cl)Cl>[CH:16]1([O:15]/[N:14]=[C:5](\[C:6]2[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=2)/[C:4]([OH:21])=[O:3])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 87416765HCID 87416765, compound

Product 1

HCID 87416813(2E)-2-cyclopentyloxyimino-2-(3,4-dichlorophenyl)acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

(E)-Cyclopentyloxyimino-(3,4-dichloro-phenyl)-acetic acid ethyl ester (332 mg, 1.01 mmol) was dissolved in ethanol (10 mL) and cooled to 0° C. A 2.0 N solution of lithium hydroxide in water (1.51 mL, 3.02 mmol) was added dropwise. The reaction mixture was allowed to gradually warm to 25° C. over 1.5 h, then diluted with chloroform (125 mL) and washed with 0.3 M potassium bisulfate solution (60 mL). The aqueous phase was extracted with chloroform (75 mL) and the combined organic phases were dried over magnesium sulfate and evaporated in vacuo to afford (E)-cyclopentyloxyimino-(3,4-dichloro-phenyl)-acetic acid as a faintly yellow semi-solid (304 mg, quant.) that was used without further purification.

Workup

  1. temperatureto gradually warm to 25° C. over 1.5 h
  2. washwashed with 0.3 M potassium bisulfate solution (60 mL)
  3. extractionThe aqueous phase was extracted with chloroform (75 mL)
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-601a4a2ed9dc49fb968f4e408731e57c
Source dataset
uspto-grants-2011_03
Patent number
US07902248B2

Reaction notes

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