Isopropyl iodide → 1-(4-(Propan-2-yloxy)phenyl)ethan-1-one

HRID 1038515Notes

Reaction equation

HRID 1038515 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=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:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1)[CH3:19]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 74694'-HydroxyacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 7340081-(4-(Propan-2-yloxy)phenyl)ethan-1-oneYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

1-(4-Hydroxyphenyl)ethanone (15.0 g, 110 mmol) was dissolved in acetone (125 mL), added sequentially with potassium carbonate (30.4 g, 220 mmol) and 1-methylethyl iodide (16.5 mL, 165 mmol), and the mixture was stirred at 70° C. for 8 hours. The reaction solution was filtered, washed with acetone and concentrated in vacuo. The obtained residue was added water and ethyl acetate, 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-[4-(1-methylethoxy)phenyl]ethanone (18.2 g (yield 93%)) was obtained as a white crystal.

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-821deb4f340d4f2c80d556261a4a3441
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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