Ethanol → Ethyl 5-acetyl-4-oxohexanoate

HRID 1761136Notes

Reaction equation

HRID 1761136 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, a 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 was added over 30 min. The mixture was refluxed for 2.5 hrs 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 through a wiped film still at 0.1 mm. The distillate was redistilled through 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, a reflux condenser, and mechanical stirring
  2. customplaced in an oil bath
  3. additionwas added over 30 min
  4. temperatureThe mixture was refluxed for 2.5 hrs
  5. customthe solvent removed by rotary evaporation
  6. filtrationThe residue was filtered through a pad of diatomaceous earth
  7. distillationdistilled through a wiped film still at 0.1 mm
  8. distillationThe distillate was redistilled through a 10 inch vacuum

Sources & evidence

ORD record
ord-695b51ad59724c47878ab6fe01689ee1
Source dataset
uspto-grants-2005_01
Patent number
US06846839B1

Reaction notes

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