Methyl iodide → 5-Acetyl-5-methyl-6-oxo-heptanoic acid ethyl ester

HRID 1375099Notes

Reaction equation

HRID 1375099 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH2:6][CH2:7][CH:8]([C:12](=[O:14])[CH3:13])[C:9](=[O:11])[CH3:10])[CH3:2].[C:16](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH2:6][CH2:7][C:8]([C:9](=[O:11])[CH3:10])([CH3:16])[C:12](=[O:14])[CH3:13])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 10104678HCID 10104678, compound

Product 1

HCID 587849645-Acetyl-5-methyl-6-oxo-heptanoic acid ethyl esterYield 87.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5.5 g of 5-acetyl-6-oxo-heptanoic acid ethyl ester, 5.7 g of potassium carbonate, 15 g of iodo-methane, and 15 ml of acetone were refluxed for 18 hours. After cooling, petroleum ether was added, and the solid was filtered off and washed with acetone and petroleum ether. Fractional distillation and re-distillation yielded 5.11 g of 5-acetyl-5-methyl-6-oxo-heptanoic acid ethyl ester (boiling point: 151° C./20 mbar; purity: 82%; colorless).

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid was filtered off
  3. washwashed with acetone and petroleum ether
  4. distillationFractional distillation and re-distillation

Sources & evidence

ORD record
ord-9ac51e868d1846bf842a3862c8eaadc1
Source dataset
uspto-grants-2007_01
Patent number
US07166648B2

Reaction notes

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