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

HRID 1749530Notes

Reaction equation

HRID 1749530 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-c98b60add5eb44b99fb6e2203ef2866b
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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