Piperidine → 3-[(4-methoxyphenyl)methylidene]pentane-2,4-dione

HRID 1915993Notes

Reaction equation

HRID 1915993 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[C:11]([CH2:14][C:15](=[O:17])[CH3:16])(=[O:13])[CH3:12].N1CCCCC1>C1CCCCC1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[C:14]([C:15](=[O:17])[CH3:16])[C:11](=[O:13])[CH3:12])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 312444-MethoxybenzaldehydeHCID 31261Acetylacetone

Product 1

HCID 2404143-[(4-methoxyphenyl)methylidene]pentane-2,4-dioneYield 70%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

3-(4-methoxybenzylidene)-2,4-pentanedione was prepared by the condensation of 4-methoxy benzaldehyde with acetyl acetone in the presence of piperidine and cyclohexane as the reaction medium at reflux temperature under continuous azeotropic water removal. The reaction takes about eight hours to complete. The reaction product was purified by crystallization with methanol and yields about 70% 3-(4-methoxybenzylidene)-2,4-pentanedione (hereinafter “Compound 3”) with a purity, as determined by GC, of about 99.6%. Compound 3 is an off-white free-flowing powder having a melting point of 82-84° C. with a λmax at 319 nm.

Workup

  1. temperatureat reflux temperature under continuous azeotropic water
  2. customremoval
  3. customThe reaction product was purified by crystallization with methanol

Sources & evidence

ORD record
ord-47be98813c9942f79417580fca1170b1
Source dataset
uspto-grants-2013_12
Patent number
US08617528B2

Reaction notes

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