Isopropyl iodide → 1-(3-isopropoxyphenyl)ethanone

HRID 1038564Notes

Reaction equation

HRID 1038564 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:17][CH:18](I)[CH3:19]>CC(C)=O>[CH3:17][CH:18]([O:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1)[CH3:19]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 84873-HydroxyacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 51728431-(3-isopropoxyphenyl)ethanoneYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

1-(3-Hydroxyphenyl)ethanone (1.36 g, 10 mmol) was dissolved in acetone (50 mL) and potassium carbonate (2.76 g, 20 mmol) and 1-methylethyl iodide (1.5 mL, 15 mmol) were added sequentially, and the mixture was stirred at 70° C. overnight. The reaction solution was filtered, washed with acetone and concentrated in vacuo. The obtained residue was added water and ethyl acetate, and extracted with ethyl acetate. The organic layer was washed with 1N aqueous solution of sodium hydroxide and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. 1-(3-(1-methylethoxy)-phenyl)ethanone (1.67 g (yield 94%)) was obtained as a yellow oil.

Workup

  1. filtrationThe reaction solution was filtered
  2. washwashed with acetone
  3. concentrationconcentrated in vacuo
  4. additionThe obtained residue was added water and ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with 1N aqueous solution of sodium hydroxide and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4dfc2f165e24422bbbca309a959ab2a9
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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