Lithium Hydroxide → 5-(2,5-Dichlorophenyl)pentanoic acid

HRID 1735649Notes

Reaction equation

HRID 1735649 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]C)=[O:14].[Li+].[OH-]>C1COCC1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 22013526Methyl 5-(2,5-Dichlorophenyl)pentanoate

Product 1

HCID 220135385-(2,5-Dichlorophenyl)pentanoic acidYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 5-(2,5-Dichlorophenyl)pentanoate (1.10 g, 4.2 mmol) was dissolved in 20 ml THF and 7 mL methanol. 1N LiOH (12mL) was added dropwise and the reaction was stirred at room temperature for 2 days. The reaction was worked-up by acidification with 2N HCl and removal of most of the THF and methanol on a rotary evaporator followed by extraction of the aqueous residue with ethyl acetate. The organic phase was washed with water and saturated brine, dried over sodium sulfate and concentrated to a residue. Flash chromatography (silica gel; hexane/toluene (19/1) with 1% acetic acid) of the residue gave 725 mg (70%) of a white solid.

Workup

  1. customThe reaction was worked-up by acidification with 2N HCl and removal of most of the THF and methanol
  2. customon a rotary evaporator
  3. extractionfollowed by extraction of the aqueous residue with ethyl acetate
  4. washThe organic phase was washed with water and saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to a residue

Sources & evidence

ORD record
ord-4fb25e87328a4b16968aa0fe7918c427
Source dataset
uspto-grants-1996_07
Patent number
US05538852

Reaction notes

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