Ethanol → Ethyl 5-acetyl-4-oxohexanoate

HRID 1815357Notes

Reaction equation

HRID 1815357 reaction equation
[CH2:1]([OH:3])[CH3:2].[Na].C[C:6](=O)[CH2:7][C:8](=[O:10])C.[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=[CH2:14]>[Na].C(O)(=O)C>[C:1]([CH:7]([CH3:6])[C:8](=[O:10])[CH2:14][CH2:13][C:12]([O:16][CH2:17][CH3:18])=[O:15])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 8821Ethyl AcrylateHCID 31261AcetylacetoneHCID 5360545Sodium

Product 1

HCID 13545064Ethyl 5-acetyl-4-oxohexanoate

Reagents, catalysts & solvents 2

HCID 5360545SodiumCatalystHCID 176Acetic AcidSolvent

Procedure

Sodium metal (1.5 g) was placed in a 3 L 3-neck round bottom flask equipped with a thermometer, reflux condenser and mechanical stirring and placed in an oil bath. Absolute ethanol (1 L) was added with stirring. When the sodium had dissolved, 350 g of pentan-2,4-dione was added all at once and then 310 g of ethyl acrylate added over 30 minutes. The mixture was refluxed for 2.5 hours and then allowed to cool to room temperature overnight. Glacial acetic acid (3 mL) was added and the solvent removed by rotary evaporation. The residue was filtered through a pad of diatomaceous earth and distilled in a wiped film still at 0.1 mm. The distillate was redistilled using a 10 inch vacuum jacketed Vigreux column to give 518 g of ethyl 5-acetyl-4-oxohexanoate, BP 84-92° C. at 0.2-0.7 mm.

Workup

  1. customequipped with a thermometer
  2. temperaturereflux condenser
  3. customplaced in an oil bath
  4. stirringwith stirring
  5. additionadded over 30 minutes
  6. temperatureThe mixture was refluxed for 2.5 hours
  7. customthe solvent removed by rotary evaporation
  8. filtrationThe residue was filtered through a pad of diatomaceous earth
  9. distillationdistilled in a wiped film still at 0.1 mm
  10. distillationThe distillate was redistilled

Sources & evidence

ORD record
ord-8fb03bff8a4946309cd0aab1867234b2
Source dataset
uspto-grants-2005_04
Patent number
US06878733B1

Reaction notes

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