Water → 1-(3,5-Dichlorophenoxy)-2-butanone

HRID 2114666Notes

Reaction equation

HRID 2114666 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[CH:9]=[C:10]([OH:15])[CH:11]=[C:12]([Cl:14])[CH:13]=1.Br[CH2:17][C:18](=[O:21])[CH2:19][CH3:20].O>CC(C)=O>[Cl:7][C:8]1[CH:9]=[C:10]([CH:11]=[C:12]([Cl:14])[CH:13]=1)[O:15][CH2:17][C:18](=[O:21])[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 115713,5-DichlorophenolHCID 131561-Bromo-2-butanone

Product 1

HCID 219497931-(3,5-Dichlorophenoxy)-2-butanoneYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Cesium carbonate (108 g, 0.33 mol) was added in one portion to a stirred solution of 3,5-dichlorophenol (49 g, 0.30 mol) in acetone (900 ml) at room temperature under nitrogen. To this suspension a solution of 1-bromo-2-butanone (30.6 ml, 0.30 mol) in acetone (300 ml) was added dropwise and the resultant suspension was heated under reflux for 2 hours. The suspension was cooled to room temperature, water (200 ml) was added and the acetone was removed under reduced pressure. The mixture was extracted with dichloromethane (2×300 ml) and the combined organic phases were dried over magnesium sulphate, filtered and concentrated under reduced pressure to leave a clear oil. The crude product was purified by flash column chromatography on silica gel eluting with dichloromethane:cyclohexane (50:50, by volume) to provide the title compound (65 g) as a yellow oil.

Workup

  1. temperatureunder reflux for 2 hours
  2. customthe acetone was removed under reduced pressure
  3. extractionThe mixture was extracted with dichloromethane (2×300 ml)
  4. dry with materialthe combined organic phases were dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto leave a clear oil
  8. customThe crude product was purified by flash column chromatography on silica gel eluting with dichloromethane:cyclohexane (50:50, by volume)

Sources & evidence

ORD record
ord-2a5aab02f2a249a0847aa4153fb385de
Source dataset
uspto-grants-2008_10
Patent number
US07435728B2

Reaction notes

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