Diethyl Carbonate → Ethyl 2-oxooctanoate

HRID 1650632Notes

Reaction equation

HRID 1650632 reaction equation
[CH2:1]([C:7](C)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:10](=[O:17])([O:14][CH2:15][CH3:16])OCC.[H-].[Na+]>O1CCOCC1>[CH2:1]([C:7](=[O:8])[C:10]([O:14][CH2:15][CH3:16])=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 80932-OctanoneHCID 24758Sodium hydride

Product 1

HCID 10888659Ethyl 2-oxooctanoateYield 62.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 20.0 g of methyl hexyl ketone in 100 ml of dioxane was dropped into a solution comprising 210 ml of diethyl carbonate, 12.8 g of sodium hydride dispersed in oil at a concentration of 60% by weight and 100 ml of dioxane in an argon atmosphere, and the mixture was refluxed overnight. Then, the solvent was removed and the residue was distilled under a reduced pressure to obtain 20.0 g of ethyl hexylketoacetate having a boiling point of 83° C. under 0.65 mmHg. The yield was 62.5%.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customThen, the solvent was removed
  3. distillationthe residue was distilled under a reduced pressure

Sources & evidence

ORD record
ord-1dab40ca37664f1db084df37ab4b3e70
Source dataset
uspto-grants-1990_05
Patent number
US04925591

Reaction notes

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