Methyl iodide → 1,2,3,4-Tetramethoxybenzene

HRID 1527670

Reaktionsgleichung

Reaktionsgleichung von HRID 1527670
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[CH:5][C:4]=1[OH:13].[C:14]([O-])([O-])=O.[K+].[K+].CI.CCOC(C)=O>CC(C)=O>[CH3:12][O:11][C:7]1[CH:6]=[CH:5][C:4]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 6035772,3,4-Trimethoxyphenol

Produkt 1

HCID 6077731,2,3,4-TetramethoxybenzeneAusbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Following the procedure by Tremblay et al.,17 17 (3.851 g, 20.9 mmol) was dissolved in dry acetone (90.0 ml), and K2CO3 (9.36 g, 67.7 mmol) was added followed by MeI (9.0 mL, 144 mmol). The reaction was heated under reflux for 26 h and monitored by TLC (1:9 EtOAc:hexanes) for completion. When complete the reaction was cooled to room temperature and filtered. The acetone was removed under reduced pressure and the residue was taken up in CH2Cl2 (50 mL). The suspension was filtered, dried over MgSO4, filtered again, and condensed. The crude product can be purified by flash chromatography (1:4 EtOAc:hexanes), however, recrystallization from Et2O/hexanes was sufficient to provide pure 18 (3.405 g, 17.2 mmol, 82%) as white needles.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 26 h
  3. filtrationfiltered
  4. customThe acetone was removed under reduced pressure
  5. filtrationThe suspension was filtered
  6. dry with materialdried over MgSO4
  7. filtrationfiltered again
  8. customcondensed
  9. customThe crude product can be purified by flash chromatography (1:4 EtOAc:hexanes)
  10. customhowever, recrystallization from Et2O/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-160a9da54c0247b199edd594e23558a2
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09089605B2

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