Butyryl chloride → Ethyl 3-oxohexanoate

HRID 1587360Notes

Reaction equation

HRID 1587360 reaction equation
C[C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])O1.[C:11](Cl)(=O)[CH2:12][CH2:13]C>ClCCl.N1C=CC=CC=1.C(O)C>[O:9]=[C:4]([CH2:11][CH2:12][CH3:13])[CH2:5][C:6]([O:7][CH2:2][CH3:10])=[O:8]

Participants

6

Reactant 2

HCID 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

Conditions

Temperature
0 °C

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 0° C. with a water/ice bath and 133 ml of butyryl chloride are added dropwise. When the addition is complete, the mixture is stirred for 3 hours at room temperature. The solution is washed with dilute hydrochloric acid solution, dried over magnesium sulphate and evaporated under vacuum to give an oil. This oil is dissolved in 700 ml of ethanol and the mixture is heated to reflux for 6 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 a liquid of boiling point b.p.20 98°-100° C.

Workup

  1. additionWhen the addition
  2. washThe solution is washed with dilute hydrochloric acid solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated under vacuum
  5. customto give an oil
  6. temperaturethe mixture is heated
  7. temperatureto reflux for 6 hours
  8. customThe ethanol is evaporated off under vacuum
  9. customthe residue obtained
  10. distillationis distilled

Sources & evidence

ORD record
ord-a74c58996abf4c7bbad3e57f1c458b83
Source dataset
uspto-grants-1993_06
Patent number
US05217973

Reaction notes

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