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

HRID 1690141Notes

Reaction equation

HRID 1690141 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). The resultant mixture was sequentially added with potassium carbonate (30.4 g, 220 mmol) and 1-methylethyl iodide (16.5 mL, 165 mmol) and then stirred at 70° C. for 8 hours. The reaction solution was filtered, washed with acetone, and concentrated in vacuo. The obtained residue was added with water and ethyl acetate, and then extracted with ethyl acetate. The organic layer was washed with 1N aqueous solution of sodium hydroxide and brine, dried using 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 with 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. customdried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0d352e5bdbb24612ba340c7b4d83d8f6
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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