Iodoethane → 1-(3-Ethoxyphenyl)ethanone

HRID 1293696Notes

Reaction equation

HRID 1293696 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([OH:10])[CH:9]=1)=[O:3].[CH2:11](I)[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:11][CH2:12][O:10][C:8]1[CH:9]=[C:4]([C:2]([CH3:1])=[O:3])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 84873-HydroxyacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 37702501-(3-Ethoxyphenyl)ethanoneYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
23 °C

Procedure

Commercially available 3-hydroxyacetophenone (25 g, 184 mmol) was stirred with ethyl iodide (17.8 mL, 220 mmol) and potassium carbonate (126.89 g, 918 mmol) in acetone (500 mL) at 55° C. for 16 h. Cooled to 23° C., filtered the solids off and the solvent was removed in vacuum. The residue was purified by silica gel column chromatography with heptane/ethyl acetate 4:1 to give the title compound as a light yellow liquid (29.5 g, 98%). MS (ISP) 165.2 [(M+H)+].

Workup

  1. filtrationfiltered the solids off and the solvent
  2. customwas removed in vacuum
  3. customThe residue was purified by silica gel column chromatography with heptane/ethyl acetate 4:1

Sources & evidence

ORD record
ord-9acfc7587fc6470cb5f2fdc3a7e87864
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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