1-(4-Chlorophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one

Synthesis

The general procedure for the synthesis of 1-(4-chlorophenyl)-3-(4-methoxyphenyl)-2-propen-1-one from p-chloroacetophenone and p-methoxybenzaldehyde was as follows: a fresh sodium methanol/methanol solution was prepared by slicing sodium metal (0.01 g, 0.4 mmol) into thin slices and adding it slowly to anhydrous methanol (15 mL) in an ice bath until no more gas was produced. Subsequently, 4-methoxybenzaldehyde (1.36 g, 10.0 mmol) was added to the freshly prepared and cooled sodium methanol/methanol solution (15 mL), followed by the slow dropwise addition of 10.0 mmol of p-chloroacetophenone. The reaction mixture was stirred at room temperature for 2-8 hours (the reaction time was extended to 36-54 hours for substrates containing naphthalene groups or other large site-blocking groups). The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, water (20 mL) and ethyl acetate (75 mL in three additions of 25 mL each) were added to the mixture. The organic phase was separated and the aqueous phase was extracted three times with ethyl acetate. The organic phases were combined, washed three times with saturated brine and dried over anhydrous sodium sulfate. The crude product was purified by silica gel column chromatography using mixed solvent of ethyl acetate/hexane as eluent to give the pure α,β-unsaturated carbonyl compound (1-(4-chlorophenyl)-3-(4-methoxyphenyl)-2-propen-1-one).

References

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[4] Medicinal Chemistry Research, 2012, vol. 21, # 6, p. 922 - 931
[5] Natural Product Research, 2015, vol. 29, # 19, p. 1804 - 1810