Benzoylacetone → 2Z-[(4-hexylphenyl)methylene]-1-phenyl-1,3-butanedione

HRID 1198214Notes

Reaction equation

HRID 1198214 reaction equation
[C:1]([CH2:9][C:10](=[O:12])[CH3:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:13]([C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>N1CCCCC1.C(OCC)C>[CH2:13]([C:19]1[CH:26]=[CH:25][C:22](/[CH:23]=[C:9](/[C:10](=[O:12])[CH3:11])\[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])=[CH:21][CH:20]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 7166Benzoylacetone2×HCID 170813Benzaldehyde, 4-hexyl-

Product 1

HCID 678204432Z-[(4-hexylphenyl)methylene]-1-phenyl-1,3-butanedione

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 3283Diethyl EtherSolvent

Procedure

Benzoylacetone (0.65g, 0.004 moles), parahexylbenzaldehyde (0.76g, 0.004 moles) and piperidine (3 drops) were stirred in ethyl ether (10ml) for 20 hrs. An additional 200mg benzoylacetone was added and the solution stirred for 48 hrs. The solution was concentrated to an oil with a gentle stream of Nitrogen. The product was purified by silica gel chromatography. The structure assignment was supported by NMR, infrared and uv spectra and elemental analysis (334.5).

Workup

  1. concentrationThe solution was concentrated to an oil with a gentle stream of Nitrogen
  2. customThe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-534fa26faf7540c49b873a3ed7cde52c
Source dataset
uspto-grants-1994_01
Patent number
US05280047

Reaction notes

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