Lithium Hydroxide → 5-(3,4-dichlorophenyl)-3-methyl-pentadienoic Acid

HRID 989781Notes

Reaction equation

HRID 989781 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]([CH3:18])=[CH:12][C:13]([O:15]CC)=[O:14])[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[Li+].O1CCOCC1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]([CH3:18])=[CH:12][C:13]([OH:15])=[O:14])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 86584516Ethyl 5-(3,4-dichlorophenyl)-3-methyl-pentadienoate

Product 1

HCID 858118935-(3,4-dichlorophenyl)-3-methyl-pentadienoic AcidYield 102.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ehtyl 5-(3,4-dichlorophenyl)-3-methyl-pentadienoate (0.120 g, 0.418 mmol) in tetrahydrofuran (0.5 mL) is treated with aqueous 1 M lithium hydroxide (0.5 mL, 0.5 mmol). The cloudy reaction mixture is treated with dioxane (1 mL). After stirring at room temperature for two days, the mixture is concentrated in vacuo. The residue is diluted with 1 M aqueous HCl and extracted several times with chloroform. The organic layers are combined, dried (sodium sulfate), and concentrated in vacuo to yield 0.110 g of a white solid, mp, 212-214° C.

Workup

  1. customThe cloudy reaction mixture
  2. concentrationthe mixture is concentrated in vacuo
  3. additionThe residue is diluted with 1 M aqueous HCl
  4. extractionextracted several times with chloroform
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-468df6991ec44f49ae05a5de5d5d000e
Source dataset
uspto-grants-2002_10
Patent number
US06458806B1

Reaction notes

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