Acetone → Ethanone, 2-iodo-1-(4-methoxyphenyl)-

HRID 1253313Notes

Reaction equation

HRID 1253313 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].[I-:13].[K+].CC(C)=O>O>[I:13][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 180AcetoneHCID 4875Potassium IodideHCID 4965Bromomethyl 4-methoxyphenyl ketone

Product 1

HCID 144919Ethanone, 2-iodo-1-(4-methoxyphenyl)-Yield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-bromo-1-(4'-methoxy-phenyl)-ethanone (22.9 g, 0.1 mol), potassium iodide (66.4 g, 0.4 mol) and acetone (200 ml) is heated at reflux for 3 h. The reaction mixture is cooled, poured into water (0.25 l) and extracted with ethyl ether (3×100 ml) The combined organic extract is washed with water and dried (Na2SO4). Evaporation of the solvent in vacuo leaves a residue which by crystallization from petroleum ether gives 2-iodo-1-(4'-methoxy-phenyl)-ethanone (22 g, 0.094 mol, yield 80%), m.p. 63°-65° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 h
  3. temperatureThe reaction mixture is cooled
  4. extractionextracted with ethyl ether (3×100 ml) The combined
  5. extractionorganic extract
  6. washis washed with water
  7. dry with materialdried (Na2SO4)
  8. customEvaporation of the solvent in vacuo
  9. customleaves a residue which
  10. customby crystallization from petroleum ether

Sources & evidence

ORD record
ord-fb7353a0857e4bc3af4dd9d29c2c5cfe
Source dataset
uspto-grants-1988_05
Patent number
US04748253

Reaction notes

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