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

HRID 1749521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749521
[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. The reaction mixture was concentrated 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. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (5-10% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-c04033cc612c47d3a17321a08e70ee1e
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156798B2

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