Methyl iodide → 4-Methylheptane-3,5-dione

HRID 132721Notes

Reaction equation

HRID 132721 reaction equation
[H-].[Na+].O1CCC[CH2:4]1.[CH3:8][CH2:9][C:10](=[O:16])[CH2:11][C:12](=[O:15])[CH2:13][CH3:14].IC>O>[CH3:4][CH:11]([C:10](=[O:16])[CH2:9][CH3:8])[C:12](=[O:15])[CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 819233,5-Heptanedione

Product 1

HCID 30139824-Methylheptane-3,5-dioneYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 0.02 mol sodium hydride was added 100 ml anhydrous tetrahydrofuran, slowly added dropwise 0.02 mol 3,5-heptandione at room temperature. Upon completion, the mixture was stirred for 0.5 hours, then 0.04 mol iodomethane was slowly added dropwise. After stirred at room temperature for 10 hours, 20 ml water was added. White solid was precipitated. The solid was filtered, washed with water, and dried to give 4-methyl-3,5-heptandione as a white solid, and the yield was 94%. m.p. was 91-92° C.

Workup

  1. stirringAfter stirred at room temperature for 10 hours
  2. customWhite solid was precipitated
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-215ad9bed3a34087a85ae1671f74959f
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Reaction notes

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