Methyl iodide → 3,3-Dimethyl-2,4-pentanedione

HRID 132717

Reaction equation

HRID 132717 reaction equation
[H-].[Na+].O1CCC[CH2:4]1.[CH3:8][CH:9]([C:13](=[O:15])[CH3:14])[C:10](=[O:12])[CH3:11].IC>O>[CH3:8][C:9]([CH3:4])([C:13](=[O:15])[CH3:14])[C:10](=[O:12])[CH3:11]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 699493-Methyl-2,4-pentanedione

Product 1

HCID 765953,3-Dimethyl-2,4-pentanedioneYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 0.1 mol sodium hydride was added 100 ml anhydrous tetrahydrofuran, and slowly added dropwise 0.12 mol 3-methyl-2,4-pentandione at room temperature. Upon completion, the mixture was stirred for 0.5 hours, then 0.12 mol iodomethane was slowly added dropwise. After stirred at room temperature for 10 hours, 20 ml water was added to dissolve solid. The mixture was extracted with ethyl acetate. The solvent was removed. Distillation was carried out under reduced pressure, and cut fraction 82-84° C./1 kPa was collected. The yield was 98%.

Workup

  1. stirringAfter stirred at room temperature for 10 hours
  2. dissolutionto dissolve solid
  3. extractionThe mixture was extracted with ethyl acetate
  4. customThe solvent was removed
  5. distillationDistillation
  6. customfraction 82-84° C./1 kPa
  7. customwas collected

Sources & evidence

ORD record
ord-da4992f5f6e34236ae9e1bcb365f26c5
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Linked notes

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