Pyridine → 2-(6-m-Methoxyphenyl-3-oxohexyl)-2-ethylcyclohexane-1,3-dione

HRID 1077137Notes

Reaction equation

HRID 1077137 reaction equation
[CH2:1]([CH:3]1[C:8](=[O:9])[CH2:7][CH2:6][CH2:5][C:4]1=[O:10])[CH3:2].N1C=CC=CC=1.C(N(CC)[CH2:20][CH2:21][C:22](=[O:34])[CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=1)C.COC1C=C(CCCC(=O)C=C)C=CC=1>C1C=CC=CC=1>[CH3:33][O:32][C:28]1[CH:27]=[C:26]([CH2:25][CH2:24][CH2:23][C:22](=[O:34])[CH2:21][CH2:20][C:3]2([CH2:1][CH3:2])[C:8](=[O:9])[CH2:7][CH2:6][CH2:5][C:4]2=[O:10])[CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 107982386-m-Methoxyphenylhex-1-en-3-oneHCID 108988052-Ethylcyclohexane-1,3-dioneHCID 214855041-(Diethylamino)-6-(3-methoxyphenyl)hexan-3-one

Product 1

HCID 214854572-(6-m-Methoxyphenyl-3-oxohexyl)-2-ethylcyclohexane-1,3-dione

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Reflux 2-ethylcyclohexane-1,3-dione (30.6 g), pyridine (20 cc), benzene (372 cc) and a mixture of 1-diethylamino-6-m-methoxyphenylhexan-3-one and 6-m-methoxyphenylhex-1-en-3-one (40.3 g, produced by the distillation of the former substance) for 15 hours. Wash the cooled reaction mixture with water, 10% aqueous sulfuric acid, water, 10% aqueous sodium carbonate, water and brine, and filter. Evaporate the solvent to leave as residue 2-(6-m-methoxyphenyl-3-oxohexyl)-2-ethylcyclohexane-1,3-dione, 38.1 g, 56.2%.

Workup

  1. customproduced by the distillation of the former substance) for 15 hours
  2. washWash
  3. customthe cooled reaction mixture with water, 10% aqueous sulfuric acid, water, 10% aqueous sodium carbonate, water and brine
  4. filtrationfilter
  5. customEvaporate the solvent

Sources & evidence

ORD record
ord-9a1d63c14bec460785155c69f39e0709
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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