Potassium Carbonate → 5'-Chloro-2'-(2-methyl-2-propenyloxy)acetophenone

HRID 416025

Reaction equation

HRID 416025 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([CH3:22])=[CH2:21]>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:21][C:20]([CH3:22])=[CH2:19])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 740613-Chloro-6-hydroxyacetophenoneHCID 3577853-Bromo-2-methyl-1-propene

Product 1

HCID 582940385'-Chloro-2'-(2-methyl-2-propenyloxy)acetophenoneYield 97.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 5′-chloro-2′-hydroxyacetophenone (0.86 g, 5.0 mmol), potassium carbonate (1.4 g, 10 mmol) and 3-bromo-2-methylpropene (0.56 mL, 5.5 mmol) in anhydrous N,N-dimethylformamide (20 mL) was stirred at 60° C. for 4 hours. After cooling, the reaction mixture was diluted with water (100 mL), and the whole was extracted with ethyl acetate (100 mL). The organic layer was washed with saturated aqueous ammonium chloride solution (50 mL) and brine (50 mL) and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give the title reference compound (1.1 g) as orange oil (Yield 96%).

Workup

  1. temperatureAfter cooling
  2. extractionthe whole was extracted with ethyl acetate (100 mL)
  3. washThe organic layer was washed with saturated aqueous ammonium chloride solution (50 mL) and brine (50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1609479122814f759c812f9af7a87ca2
Source dataset
uspto-grants-2012_01
Patent number
US08088817B2

Linked notes

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