Acetic Acid → Methyl 2-(2,6-dichlorophenylmethylidene)-3-oxo-5-phenylpentanoate

HRID 342505Notes

Reaction equation

HRID 342505 reaction equation
[O:1]=[C:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:3][C:4]([O:6][CH3:7])=[O:5].[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:18]=1[CH:19]=O.C(O)(=O)C.N1CCCCC1>C1C=CC=CC=1.O>[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:18]=1[CH:19]=[C:3]([C:2](=[O:1])[CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 67372,6-DichlorobenzaldehydeHCID 8082PiperidineHCID 561998Methyl 3-oxo-5-phenylpentanoate

Product 1

HCID 53937813Methyl 2-(2,6-dichlorophenylmethylidene)-3-oxo-5-phenylpentanoate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 3-oxo-5-phenylpentanoate (10 g, 48.5 mmol), 2,6-dichlorobenzaldehyde (8.486 g, 48.5 mmol), acetic acid (0.56 ml, 9.7 mmol), and piperidine (0.24 ml, 2.42 mmol) in benzene (100 ml) was refluxed with azeotropic removal of water for 3 h. After cooled down, the reaction mixture was wash with water, NaHCO3 aqueous solution, and brine, and dried over Na2SO4. Evaporation of the solvent afforded crude viscous oil, which was used for next reaction without purification. 1H NMR data indicated that this was 1:1 mixture of E and Z isomers.

Workup

  1. temperatureAfter cooled down
  2. washthe reaction mixture was wash with water, NaHCO3 aqueous solution, and brine
  3. dry with materialdried over Na2SO4
  4. customEvaporation of the solvent
  5. customafforded crude viscous oil, which
  6. customwas used for next reaction without purification
  7. addition1:1 mixture of E and Z isomers

Sources & evidence

ORD record
ord-1fce6f99968c41e9a9d85b674a91adc6
Source dataset
uspto-grants-1999_01
Patent number
US05859011

Reaction notes

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