Methyl iodide → 2,2-Dimethyl-1,3-cyclohexanedione

HRID 1749530Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749530
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.[C:9](=[O:12])([O-])[O-].[K+].[K+].I[CH3:16]>CC(C)=O>[CH3:16][C:2]1([CH3:1])[C:3](=[O:7])[CH2:4][CH2:5][CH2:6][C:9]1=[O:12]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 104341,3-CyclohexanedioneHCID 11430Potassium Carbonate

Produkt 1

HCID 5509672,2-Dimethyl-1,3-cyclohexanedioneAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of cyclohexane-1,3-dione (10.0 g, 89.3 mmol), potassium carbonate (24.6 g, 178.6 mmol) and iodomethane (28.5 g, 201 mmol) in acetone (50 mL) was refluxed overnight. After completion, the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (5-10% ethyl acetate in petroleum ether) to afford the title compound (3.5 g, 25.0 mmol, 28% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 2.69 (t, J=6.8 Hz, 4H), 1.52 (m, 2H) 1.31 (s, 6H).

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. customAfter completion, the solvent was removed under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (5-10% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-c98b60add5eb44b99fb6e2203ef2866b
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156798B2

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