2-Hexanone → Ethyl 3-oxoheptanoate

HRID 1602944Notes

Reaction equation

HRID 1602944 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.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

9

Reactant 4

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

Product 1

HCID 559036Ethyl 3-oxoheptanoateYield 193.9%

Reagents, catalysts & solvents 4

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

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 (50% in oil, washed 3 times with hexane) in 250 ml of ether and the mixture was stirred for 10 minutes and 30 g of hexanone were added. The mixture was refluxed for 2 hours and then a solution of 35 ml of ether containing 12 ml of ethanol was added. The solution was cooled to 0° C. and a solution of 36 ml of acetic acid in 300 ml of water was added. 12 ml of a saturated sodium bicarbonate solution were added and extraction was carried out with ether. The extracts were washed with water, dried, filtered and evaporated to dryness under reduced pressure to obtain 100 g of an oil which was distilled under a pressure of 3 mbar at 70° C. to obtain 32.5 g of the desired product.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. extractionextraction
  3. washThe extracts were washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f71b241d46c3449e94e3c9c5f4373c4a
Source dataset
uspto-grants-1999_11
Patent number
US05985894

Reaction notes

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