Acetic Acid → HCID 54274945, compound

HRID 1649399Notes

Reaction equation

HRID 1649399 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][C:6]([CH2:8][Cl:9])=[O:7])[CH3:2].[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1.CCOCC.O>[CH2:1]([O:3][C:4](=[O:10])[C:5](=[CH:16][C:15]1[CH:18]=[CH:19][C:12]([Cl:11])=[CH:13][CH:14]=1)[C:6](=[O:7])[CH2:8][Cl:9])[CH3:2]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 8082PiperidineHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 54274945HCID 54274945, compoundYield 23.4%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

25.7 g of 4-chloroacetoacetic acid ethyl ester, 23.9 g of 4-chlorobenzaldehyde, 0.7 ml of piperidine and 18 ml of glacial acetic acid were dissolved in 15 ml of benzene. The solution was boiled for 5 hours, using a water separator, and was allowed to cool, and 300 ml of ether were added. After the mixture had been washed three times with water, it was dried over magnesium sulphate and the solvent was evaporated off. The residue was distilled under a high vacuum. The product obtained was a Z/E mixture in a ratio of 3/1. Yield: 23.4%, boiling point 0.5: 161° to 165°.

Workup

  1. temperatureto cool
  2. washAfter the mixture had been washed three times with water, it
  3. dry with materialwas dried over magnesium sulphate
  4. customthe solvent was evaporated off
  5. distillationThe residue was distilled under a high vacuum
  6. customThe product obtained
  7. custom161° to 165°

Sources & evidence

ORD record
ord-391a58751e614cc18a22de479af3d750
Source dataset
uspto-grants-1983_11
Patent number
US04416880

Reaction notes

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