Dichloromethane → tert-Butyl 3-oxononanoate

HRID 1449502Notes

Reaction equation

HRID 1449502 reaction equation
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])O1.[C:11](Cl)(=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].Cl[CH2:20]Cl>N1C=CC=CC=1>[O:5]=[C:4]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:6][C:7]([O:9][C:2]([CH3:1])([CH3:10])[CH3:20])=[O:8]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 67340Hexanoyl chloride

Product 1

HCID 12425369tert-Butyl 3-oxononanoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a mixture of 100 ml of dichloromethane and 32 ml of pyridine was dissolved 25.0 g of meldrum's acid. Under cooling with ice, 10.0 g of hexanoyl chloride was added dropwise to the solution, followed by stirring under room temperature for 1 hour. The solvent was removed and to the residue was added water. The mixture was extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was dissolved in 100 ml of tert-butanol, followed by reflux under heating for 3 hours. The solvent was removed under reduced pressure. The residue was subjected to distillation under reduced pressure to yield 22.0 g of the oily titled compound.

Workup

  1. additionwas added dropwise to the solution
  2. customThe solvent was removed and to the residue
  3. additionwas added water
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe extract was washed with 1N hydrochloric acid
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. dissolutionthe residue was dissolved in 100 ml of tert-butanol
  9. temperatureby reflux
  10. temperatureunder heating for 3 hours
  11. customThe solvent was removed under reduced pressure
  12. distillationThe residue was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-6f93a22158814cea927b59dc8019aace
Source dataset
uspto-grants-1997_02
Patent number
US05599813

Reaction notes

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