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

HRID 1749521Notes

Reaction equation

HRID 1749521 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. 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).

Workup

  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)

Sources & evidence

ORD record
ord-c04033cc612c47d3a17321a08e70ee1e
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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