2-Hexanone → Ethyl 3-oxoheptanoate

HRID 2260818Notes

Reaction equation

HRID 2260818 reaction equation
[C:1](=[O:6])([O-])[O:2][CH2:3][CH3:4].[H-].[Na+].[CH3:9][C:10](=[O:15])[CH2:11][CH2:12][CH2:13][CH3:14].C(=O)(O)[O-].[Na+]>CCOCC.CCCCCCC.O.C(O)(=O)C.C(O)C>[O:15]=[C:10]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:9][C:1]([O:2][CH2:3][CH3:4])=[O:6]

Participants

10

Reactant 4

HCID 115832-HexanoneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 21226545CID 21226545

Product 1

HCID 559036Ethyl 3-oxoheptanoateYield 63%

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×HCID 8900HeptaneSolvent

Conditions

Temperature
0 °C

Procedure

70.8 g of ethyl carbonate in solution in 50 ml of ether were added to a suspension of 27.3 g of sodium hydride at 50% in oil (washed beforehand in heptane) and 250 ml of ether and the mixture was stirred for 10 minutes. 30 g of hexanone were added over 30 minutes and the mixture was refluxed for 2 hours. 35 ml of ether with 12 ml of ethanol were added and the mixture was stirred for 16 hours at ambient temperature. After cooling to 0° C., a solution of 36 ml of acetic acid in 300 ml of water, then 12 ml of a saturated sodium bicarbonate solution were added, and the pH was 7. Extraction was carried out with ether and the extracts were washed with water, dried and evaporated to dryness. After distillation to 70° C. under a reduced pressure of 7 mbar, 32.5 g of the desired product were obtained.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. stirringthe mixture was stirred for 16 hours at ambient temperature
  3. extractionExtraction
  4. washthe extracts were washed with water
  5. customdried
  6. customevaporated to dryness
  7. distillationAfter distillation to 70° C. under a reduced pressure of 7 mbar

Sources & evidence

ORD record
ord-cb597a0d6c81441fb99e467340aa1758
Source dataset
uspto-grants-1995_12
Patent number
US05478938

Reaction notes

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