2,4-Dichlorophenol → HCID 23349979, compound

HRID 2058195Notes

Reaction equation

HRID 2058195 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].Br[CH2:11][C:12](=[O:18])[C:13]([O:16][CH3:17])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:11][C:12](=[O:18])[C:13]([O:16][CH3:17])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 84492,4-DichlorophenolHCID 11430Potassium CarbonateHCID 1278370276336-55-5

Product 1

HCID 23349979HCID 23349979, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
-20 °C

Procedure

A stirred mixture of 13.04 g (0.08 mole) of 2,4-dichlorophenol, 15.61 g (0.08 mole) 1-bromo-3-methoxy-3-methyl-2-butanone, and 11.1 g (0.08 mole) powdered potassium carbonate in 300 ml acetonitrile was heated at reflux temperature for 30 minutes. The reaction mixture was cooled, filtered, and the solvent evaporated from the filtrate. The residual oil was taken up in hexane and cooled to -20° C., whereupon the product separated as a white crystalline solid. There was thus obtained 19 g (85.7% yield) of 1-(2,4-dichlorophenoxy)-3-methoxy-3-methyl-2-butanone, m.p. 45.5°-47.5° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 30 minutes
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customthe solvent evaporated from the filtrate
  6. customseparated as a white crystalline solid

Sources & evidence

ORD record
ord-94e719e0b8644da6af17b1cdb3e70968
Source dataset
uspto-grants-1980_07
Patent number
US04215127

Reaction notes

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