Piperidine → 3-(3,4-dimethoxybenzylidene)-2,4-pentanedione

HRID 1915992Notes

Reaction equation

HRID 1915992 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.[C:13]([CH2:16][C:17](=[O:19])[CH3:18])(=[O:15])[CH3:14].N1CCCCC1>C1CCCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=[C:16]([C:17](=[O:19])[CH3:18])[C:13](=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 8419VeratraldehydeHCID 31261Acetylacetone

Product 1

HCID 12379903-(3,4-dimethoxybenzylidene)-2,4-pentanedione

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

3-(3,4-dimethoxybenzylidene)-2,4-pentanedione (hereinafter “Compound 2”) was prepared by the condensation of 3,4-dimethoxy 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. The typical yield of Compound 2 is about 67% with a purity, as determined by GC, of about 99.5%. Compound 2 is an off-white free-flowing powder having a melting point of 104-108° C. with a λmax at 335 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-6b2553c8a4104da79afd70516e0aba02
Source dataset
uspto-grants-2013_12
Patent number
US08617528B2

Reaction notes

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