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

HRID 343312Notes

Reaction equation

HRID 343312 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 cooling down the mixture, the whole was washed with water, NaHCO3 aqueous solution, and brine. The mixture was dried over Na2SO4 and evaporation of the solvent afforded a crude viscous oil, which was used for subsequent reaction without purification. 1H NMR data indicated that this was 1:1 mixture of E and Z isomers. 1H NMR (CDCl3) δ 7.56 and 7.60 (each s, total 1H), 7.20 (m, 8H), 3.59 and 3.83 (each s, total 3H), 3.14-2.83 (m, 4H),.

Workup

  1. temperatureAfter cooling down the mixture
  2. washthe whole was washed with water, NaHCO3 aqueous solution, and brine
  3. dry with materialThe mixture was dried over Na2SO4 and evaporation of the solvent
  4. customafforded a crude viscous oil, which
  5. customwas used for subsequent reaction without purification
  6. addition1:1 mixture of E and Z isomers

Sources & evidence

ORD record
ord-e9f4d455fe0e468fb93b8411bea26f82
Source dataset
uspto-grants-1999_01
Patent number
US05861402

Reaction notes

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