Ethanol → Ethyl 4-iodobenzoate

HRID 1222

Reaktionsgleichung

Reaktionsgleichung von HRID 1222
[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 and 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
  8. distillationthe residue kugelrohr distilled (100 degrees C.; 0.55 mm)

Quellen und Nachweise

ORD-Eintrag
ord-6724f220dc7c4e89ac64b79ac6a33d74
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723620

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