Isopropyl iodide → 1-(3-isopropoxyphenyl)ethanone

HRID 1690191Notes

Reaction equation

HRID 1690191 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 the resultant mixture was sequentially added with potassium carbonate (2.76 g, 20 mmol) and 1-methylethyl iodide (1.5 mL, 15 mmol), and stirred at 70° C. overnight. The reaction solution was filtered, washed with acetone, and concentrated in vacuo. The resultant residue was added with water and ethyl acetate and 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-(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 resultant 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-70a4a854f3314b758e000aab99760b8c
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

Loading…