Dimethyl Sulfate → Methyl 4-iodo-3-methoxybenzoate

HRID 471819

Reaktionsgleichung

Reaktionsgleichung von HRID 471819
O[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[I:11])[C:5]([OH:7])=[O:6].[C:12](=O)([O-])[O-].[K+].[K+].S([O:23][CH3:24])(OC)(=O)=O>CC(C)=O>[I:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([O:7][CH3:12])=[O:6])=[CH:3][C:2]=1[O:23][CH3:24]

Komponenten

5

Edukt 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 7368543-Hydroxy-4-iodobenzoic acid

Produkt 1

HCID 11243290Methyl 4-iodo-3-methoxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 3-hydroxy-4-iodobenzoic acid (3.0 g, 0.011 mol) in acetone (50 mL) was added in one portion potassium carbonate (3.9 g, 0.028 mol). Dimethyl sulfate (3.5 g, 0.028 mol) was added dropwise and the mixture was heated at reflux overnight. The mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and aqueous saturated sodium bicarbonate solution. The organic phase was washed with brine, dried over sodium sulfated and concentrated in vacuo to give methyl 4-iodo-3-(methyloxy)benzoate as a yellow oil. 1H NMR (DMSO-d6) δ ppm 3.83 (s, 3H, Me), 3.87 (s, 3H, Me), 7.30 (dd, J=8.0, 1.8 Hz, 1H, Ar), 7.40 (d, J=1.7 Hz, 1H, Ar), 7.92 (d, J=8.0 Hz, 1H, Ar).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was partitioned between ethyl acetate and aqueous saturated sodium bicarbonate solution
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cdc3ee586150463f95362a338a50655d
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633175B2

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