Water → Ethyl 3-oxohexanoate

HRID 274243Notes

Reaction equation

HRID 274243 reaction equation
C[C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])O1.O.[C:12](Cl)(=O)[CH2:13][CH2:14]C>ClCCl.N1C=CC=CC=1.C(O)C>[O:9]=[C:4]([CH2:12][CH2:13][CH3:14])[CH2:5][C:6]([O:7][CH2:2][CH3:10])=[O:8]

Participants

7

Reactant 3

HCID 962WaterHCID 8855Butyryl chlorideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 238498Ethyl 3-oxohexanoate

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

176 g of 2,2-dimethyl-4,6-dioxo-1,3-dioxane (Meldrum's acid) are dissolved in 550 ml of dichloromethane and 188 ml of pyridine; the mixture is cooled to 5° C. with a bath of water and ice and 133 ml of butyryl chloride are added dropwise. When the addition is complete, the mixture is stirred for three hours at room temperature. The solution is washed with a dilute solution of hydrochloric acid, dried over magnesium sulfate and evaporated under vacuum to give an oil. This oil is dissolved in 700 ml of ethanol and the mixture is refluxed for six hours. The ethanol is evaporated off under vacuum and the residue obtained is distilled to give 145.4 g of ethyl 3-oxohexanoate in the form of an oil.

Workup

  1. additionare added dropwise
  2. additionWhen the addition
  3. washThe solution is washed with a dilute solution of hydrochloric acid
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under vacuum
  6. customto give an oil
  7. temperaturethe mixture is refluxed for six hours
  8. customThe ethanol is evaporated off under vacuum
  9. customthe residue obtained
  10. distillationis distilled

Sources & evidence

ORD record
ord-ea652598a0374d4c987af1e26cea3788
Source dataset
uspto-grants-1995_02
Patent number
US05389632

Reaction notes

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