Methyl iodide → 3,6-Dimethylheptane-2,4-dione

HRID 132738

Reaction equation

HRID 132738 reaction equation
[H-].[Na+].O1CCC[CH2:4]1.[CH3:8][CH:9]([CH3:17])[CH2:10][C:11](=[O:16])[CH2:12][C:13](=[O:15])[CH3:14].IC>O>[CH3:4][CH:12]([C:11](=[O:16])[CH2:10][CH:9]([CH3:17])[CH3:8])[C:13](=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 763542,4-Heptanedione, 6-methyl-

Product 1

HCID 5382833,6-Dimethylheptane-2,4-dioneYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 0.1 mol sodium hydride was added 100 ml anhydrous tetrahydrofuran, then added slowly dropwise 0.1 mol 6-methyl-2,4-heptandione at room temperature. The reaction was stirred for 0.5 hours, then 0.12 mol iodomethane was added dropwise and the reaction was stirred at room temperature for further 10 hours. Upon completing the reaction, 20 ml water was added. The mixture was extracted with ethyl acetate. After removing the solvent, distillation under reduced pressure gave a cut fraction 88-9° C./1 kPa (165-166° C. at atmosphere pressure), and the yield was 94%.

Workup

  1. stirringthe reaction was stirred at room temperature for further 10 hours
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate
  4. customAfter removing
  5. distillationthe solvent, distillation under reduced pressure
  6. customgave a cut fraction 88-9° C./1 kPa (165-166° C. at atmosphere pressure)

Sources & evidence

ORD record
ord-bd5b8d7ad93241e686914bdcd1e363f5
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Linked notes

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