3,4-Dichlorophenol → HCID 18402082, compound

HRID 1018720Notes

Reaction equation

HRID 1018720 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+].Cl[CH:17]([C:23]([CH3:25])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[O:9][CH:17]([C:23](=[O:24])[CH3:25])[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 72583,4-DichlorophenolHCID 11430Potassium CarbonateHCID 11858Ethyl 2-chloroacetoacetate

Product 1

HCID 18402082HCID 18402082, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

13.0 g (80 mmol) of 3,4-dichlorophenol and 12.2 g (88 mmol) of potassium carbonate were refluxed for 30 minutes in 400 ml of acetone. 15.8 g (96 mmol) of ethyl 2-chloroacetoacetate were subsequently added dropwise, the mixture was refluxed for 8 hours and evaporated in vacuo, and water was added to the residue. The aqueous phase was extracted three times with ethyl acetate, and the combined organic phases were dried over magnesium sulfate and evaporated. Column chromatography of the residue gave 15.8 g (68% of theory) of ethyl 2-(3,4-dichlorophenoxy)-3-ketobutanate as an oil.

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. customevaporated in vacuo, and water
  3. additionwas added to the residue
  4. extractionThe aqueous phase was extracted three times with ethyl acetate
  5. dry with materialthe combined organic phases were dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-3965a3245ebc4ae6b5054a135683da7e
Source dataset
uspto-grants-2002_11
Patent number
US06482947B1

Reaction notes

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