2,4-Dichlorophenol → HCID 57719572, compound

HRID 1985409Notes

Reaction equation

HRID 1985409 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[H-].[Na+].C([C:14]1(Br)[CH:18]([CH3:19])[O:17][C:15]1=[O:16])C>CN(C)C=O.[Cl-].[NH4+]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][CH:14]1[CH2:18][CH2:19][O:17][C:15]1=[O:16]

Participants

6

Reactant 3

HCID 84492,4-DichlorophenolHCID 24758Sodium hydrideHCID 86760881HCID 86760881, compound

Product 1

HCID 57719572HCID 57719572, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

1 g of 2,4-Dichlorophenol was dissolved in 10 ml of N,N-dimethylformamide, and 0.27 g of 60% sodium hydride was added thereto under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. 0.7 ml of Ethylα-bromo-β-butyrolactone was added to the mixture which was then stirred at room temperature for another 1 hour. The reaction solution was diluted with aqueous ammonium chloride, and extracted with ethylacetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was subjected to silica gel column chromatography, to give 1 g of the title compound.

Workup

  1. temperatureunder ice-cooling
  2. stirringwas then stirred at room temperature for another 1 hour
  3. extractionextracted with ethylacetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1cec188c9e7b4e4a963b004c63fde985
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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