3,4,5-Trimethoxybenzaldehyde → Trimethoxybenzylidene pentanedione

HRID 1915991Notes

Reaction equation

HRID 1915991 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=O.[C:15]([CH2:18][C:19](=[O:21])[CH3:20])(=[O:17])[CH3:16].N1CCCCC1>C1CCCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=[C:18]([C:19](=[O:21])[CH3:20])[C:15](=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 8082PiperidineHCID 31261Acetylacetone

Product 1

HCID 67772502Trimethoxybenzylidene pentanedione

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

3-(3,4,5-trimethoxybenzylidene)-2,4-pentanedione (hereinafter “HSS”) was prepared by the condensation of 3,4,5-trimethoxy 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 HSS is about 68% with a purity, as determined by GC, of 99.1%. HSS is an off-white free-flowing powder with a melting point of 83-86° 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-72946f87abbe4ad595c6c987876149ea
Source dataset
uspto-grants-2013_12
Patent number
US08617528B2

Reaction notes

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