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

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Reaction Steps

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),.

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