Benzaldehyde → 5-Hexene-2,4-dione, 6-phenyl-

HRID 1915990Notes

Reaction equation

HRID 1915990 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([CH2:12][C:13](=[O:15])[CH3:14])(=[O:11])[CH3:10].N1CCCCC1>C1CCCCC1>[CH:1](=[CH:14][C:13](=[O:15])[CH2:12][C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8082PiperidineHCID 31261Acetylacetone

Product 1

HCID 27848595-Hexene-2,4-dione, 6-phenyl-

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Theses compounds may be prepared by various methods but are most conveniently prepared by reacting a benzaldehyde with acetyl acetone in the presence of a suitable catalyst and reaction medium, preferably piperidine and cyclohexane, at reflux temperature under continuous azeotropic water removal. The benzaldehyde reactant will be that which corresponds to the desired substitution of the benzylidene derivative of the final benzylidene pentanedione. The crude product resulting from the foregoing reaction may then be purified by crystallization with methanol to produce the desired benzylidene 2,4-pentanedione. Suitable reactions and reaction conditions are set forth in the examples contained herein.

Workup

  1. customTheses compounds may be prepared by various methods
  2. customare most conveniently prepared
  3. temperatureat reflux temperature under continuous azeotropic water
  4. customremoval
  5. customThe crude product resulting from the foregoing reaction
  6. custommay then be purified by crystallization with methanol

Sources & evidence

ORD record
ord-1f17ea3c47c7429981f3af814f2ab27e
Source dataset
uspto-grants-2013_12
Patent number
US08617528B2

Reaction notes

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