Acetic Acid → HCID 297403, compound

HRID 1440784Notes

Reaction equation

HRID 1440784 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:10]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:11][C:12]([CH3:14])=[O:13].C(O)(=O)C>C1C=CC=CC=1.N1CCCCC1>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[C:11]([C:12]([CH3:14])=[O:13])[C:10]([O:16][CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 69962-ChlorobenzaldehydeHCID 8868Ethyl Acetoacetate

Product 1

HCID 297403HCID 297403, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 25.0 g of 2-chlorobenzaldehyde, 23.1 g of ethyl acetoacetate, 2.1 g of acetic acid and 0.6 g of piperidine in 100 cc of benzene was heated under reflux for 8 hours and removed water by a Dean-Stark trap. After cooling, to the reaction mixture was added ethylacetate and water. The organic layer was further washed with a saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was distilled off and the crude product thus obtained was purified by a silica gel column chromatography (eluent: ethyl acetate/hexane=1/9) to obtain 44.0 g of compound A. Yield: 97.9%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 8 hours
  3. customremoved water by a Dean-Stark trap
  4. temperatureAfter cooling, to the reaction mixture
  5. additionwas added ethylacetate and water
  6. washThe organic layer was further washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled off
  9. customthe crude product thus obtained
  10. customwas purified by a silica gel column chromatography (eluent: ethyl acetate/hexane=1/9)

Sources & evidence

ORD record
ord-68f4ca5e872949d6bcac812ee1701a1a
Source dataset
uspto-grants-1996_03
Patent number
US05500424

Reaction notes

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