Methyl iodide → HCID 20467226, compound

HRID 1903399Notes

Reaction equation

HRID 1903399 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:14](=[O:15])[CH2:13][C:12](C)(C)[CH2:11][C:10]1=[O:18].[C:19](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[CH3:19][O:18][C:10]1[CH2:11][CH2:12][CH2:13][C:14](=[O:15])[C:9]=1[C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 125563452-(2,4-Dimethylphenyl)-5,5-dimethylcyclohexane-1,3-dione

Product 1

HCID 20467226HCID 20467226, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 10.00 g (0.0409 mol) of 2-(2',4'-dimethylphenyl)-5,5-dimethyl-1,3-cyclohexanedione, 21.42 g (0.155 mol) of anhydrous potassium carbonate, 17.59 g (0.124 mol) iodomethane, and 500 ml of anhydrous acetone was refluxed overnight. The reaction mixture was then cooled to room temperature, filtered, and the acetone removed. The residual solid was taken up in 250 ml of CH2Cl2, washed with water, 0.25 N NaOH, 1 N HCl, and water again. The solution was dried (MgSO4) and the solvent removed. The resulting solid was recrystallized from isopropyl ether to give 7.60 g (72% yield) of a white crystalline solid, m.p. 122°-23° C. The compound prepared by the above synthesis has the following structure: ##STR27##

Workup

  1. filtrationfiltered
  2. customthe acetone removed
  3. washwashed with water, 0.25 N NaOH, 1 N HCl, and water again
  4. dry with materialThe solution was dried (MgSO4)
  5. customthe solvent removed
  6. customThe resulting solid was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-a5695464ff6e45d88b66e8064a6e822f
Source dataset
uspto-grants-1984_03
Patent number
US04436666

Reaction notes

Loading…