Ethanol → Ethyl 4-iodobenzoate

HRID 53313

Reaktionsgleichung

Reaktionsgleichung von HRID 53313
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH2:15](O)[CH3:16]>>[CH2:15]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([I:1])=[CH:3][CH:4]=1)[CH3:16]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 120854-Iodobenzoic acidHCID 24386Thionyl Chloride

Produkt 1

HCID 142891Ethyl 4-iodobenzoate

Versuchsvorschrift

To a suspension of 10 g (40.32 mmol) of 4-iodobenzoic acid in 100 ml absolute ethanol was added 2 ml thionyl chloride and the mixture was then heated at reflux for 3 hours. Solvent was removed in vacuo and the residue was dissolved in 100 ml ether. The ether solution was washed with saturated NaHCO3 and saturated NaCl solutions and dried (MgSO4). Solvent was then removed in vacuo an the residue Kugelrohr distilled (100 degrees C; 0.55 mm) to give the title compound as a colorless oil, PMR (CDCl3): δ1.42 (3H, t, J~7 Hz), 4,4 (2H, q, J~7 Hz), 7.8 (4H).

Aufarbeitung

  1. temperaturethe mixture was then heated
  2. temperatureat reflux for 3 hours
  3. customSolvent was removed in vacuo
  4. dissolutionthe residue was dissolved in 100 ml ether
  5. washThe ether solution was washed with saturated NaHCO3 and saturated NaCl solutions
  6. dry with materialdried (MgSO4)
  7. customSolvent was then removed in vacuo an the residue Kugelrohr
  8. distillationdistilled (100 degrees C; 0.55 mm)

Quellen und Nachweise

ORD-Eintrag
ord-31c1b48112384f5e9baba133eade9567
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05618943

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