Methyl iodide → 1,3-Cyclohexanedione, 2,5,5-trimethyl-

HRID 1421650Notes

Reaction equation

HRID 1421650 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[CH2:3]1.[CH3:11]C(C)([O-])C.[K+].CI>C(O)(C)(C)C>[CH3:11][CH:6]1[C:4](=[O:5])[CH2:3][C:2]([CH3:10])([CH3:1])[CH2:9][C:7]1=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 31358DimedoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 1369011,3-Cyclohexanedione, 2,5,5-trimethyl-

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

28.0 g (0.2 mol) of dimedone were dissolved in 150 ml of absolute t-butanol and, at 40° C., 22.4 g (0.2 mol) of potassium t-butoxide were added a little at a time. After 2 hours, an equimolar amount of methyl iodide was added. After a further 2 hours, the solvent was removed under reduced pressure and the residue which remained was extracted 3 times with diethyl ether. The combined ether extracts were evaporated to dryness. Yield: 26.2 g (85%). The crude product was not purified further.

Workup

  1. waitAfter a further 2 hours
  2. customthe solvent was removed under reduced pressure
  3. extractionthe residue which remained was extracted 3 times with diethyl ether
  4. customThe combined ether extracts were evaporated to dryness
  5. customThe crude product was not purified further

Sources & evidence

ORD record
ord-32dc253c55404eaea20bbd9d01772a14
Source dataset
uspto-grants-2000_06
Patent number
US06077965

Reaction notes

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