Isopropanol → Propan-2-yl 4-iodobenzoate

HRID 2294960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2294960
S(Cl)(Cl)=O.[I:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1.[CH:15](O)([CH3:17])[CH3:16]>>[CH:15]([O:11][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][C:6]([I:5])=[CH:7][CH:8]=1)([CH3:17])[CH3:16]

Komponenten

4

Edukt 3

HCID 3776IsopropanolHCID 120854-Iodobenzoic acidHCID 24386Thionyl Chloride

Produkt 1

HCID 13975019Propan-2-yl 4-iodobenzoate

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Thionyl chloride (1.4 ml) was added to a solution of 4-iodobenzoic acid (3.72 g) in isopropanol (25 ml) and the reaction mixture heated at 50° C. for several hours. The reaction mixture was cooled to ambient temperature and evaporated. Methylene chloride was added to the residue and the mixture filtered. The filtrate was washed with saturated sodium bicarbonate solution, water, saturated brine, dried (MgSO4) and evaporated to give isopropyl-4-iodo-benzoate as an oil (1.5 g); NMR: 1.28-137(6H,d), 5.04-5.21(1H,m), 7.65-7.74(2H,d), 7.88-7.95(2H,d); m/z 291(M+H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customevaporated
  3. additionMethylene chloride was added to the residue
  4. filtrationthe mixture filtered
  5. washThe filtrate was washed with saturated sodium bicarbonate solution, water, saturated brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-09d42a93a2af49f6a37dd8e0483dc8e7
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05691349

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