1-(4-Chlorophenyl)-3-(4-methoxyphenyl)-2-propen-1-one

General procedure: Na (0.01 g, 0.4 mmol) was cut to pieces and added into anhydrous MeOH (15 mL) under ice bath; the fresh MeONa/MeOH solution was prepared till no gas evolved. 4-Methoxybenzaldehyde (1.36 g, 10.0 mmol) was added to the fresh, cooled MeONa/MeOH solution (15 mL), and then 10.0 mmol acetyl aromatic compound was added dropwise. The mixture was stirred at room temperaturefor2–8 h(36–54 hfor2nand2oduetothesteric hindrance of thenaphthyl andbiphenyl). Theend ofthereaction was monitored by TLC. Afterward, water (20 mL) and EtOAc (75 mL, 25 mL × 3) were added into the mixture. Theinorganic precipitatewas removed, and theorganic solution was washed with brine three times and dried. The crude product was puried by silica gel column chromatography with EtOAc/hexane as eluent to get pureα, β-unsaturated carbonyl compounds (2a–2o).General procedure: The target compounds were synthesised in accordance with the reaction shown in Figures 1 and 2. Appropriate aldehyde (0.01 mol) and acetophenone derivatives (0.01 mol) were dissolved in anhydrous ethanol (15 mL). The reaction mixture was stirred at 0 °C for 8 h. Then, 10percent NaOH (5 mL) was slowly added to the above mixture under stirring until the reaction was complete. The precipitate was filtered and washed with still water. The pure compounds were obtained by re-crystallisation in acetone and water.General procedure: To acetophenone (1 mmol) catalyst STA (0.1 mmol or 10 mol percent) was dissolved by stirring for 5-10 min. and further to this 4-chlorobenzaldehyde (1 mmol) was added and the mixture was magnetically stirred at room temperature until the completion of the reaction as confirmed by TLC. After the completion of the reaction the crude product was separated out, and then washed with water. The solid was filtered and dried. The crude product was further purified by recrystallization. All the products were characterised by their melting point, IR and General procedure: A mixture of α, β-unsaturated acid chloride (501 mg, 3 mmol), an aromatic compound (324 mg, 3 mmol) and zinc oxide (120 mg, 1.5 mmol) was stirred at room temperature (25–30 °C) for the specified time (Table 2). The progress of the reaction was monitored by TLC. After completion of the reaction, the product was extracted with dichloromethane (3 × 5 mL), and extract was washed with aq. NaHCOGeneral procedure: Na (0.01 g, 0.4 mmol) was cut to pieces and added into anhydrous MeOH (15 mL) under ice bath; the fresh MeONa/MeOH solution was prepared till no gas evolved. 4-Methoxybenzaldehyde (1.36 g, 10.0 mmol) was added to the fresh, cooled MeONa/MeOH solution (15 mL), and then 10.0 mmol acetyl aromatic compound was added dropwise. The mixture was stirred at room temperaturefor2-8 h(36-54 hfor2nand2oduetothesteric hindrance of thenaphthyl andbiphenyl). Theend ofthereaction was monitored by TLC. Afterward, water (20 mL) and EtOAc (75 mL, 25 mL × 3) were added into the mixture. Theinorganic precipitatewas removed, and theorganic solution was washed with brine three times and dried. The crude product was puried by silica gel column chromatography with EtOAc/hexane as eluent to get purealpha, beta-unsaturated carbonyl compounds (2a-2o).General procedure: The target compounds were synthesised in accordance with the reaction shown in Figures 1 and 2. Appropriate aldehyde (0.01 mol) and acetophenone derivatives (0.01 mol) were dissolved in anhydrous ethanol (15 mL). The reaction mixture was stirred at 0 C for 8 h. Then, 10% NaOH (5 mL) was slowly added to the above mixture under stirring until the reaction was complete. The precipitate was filtered and washed with still water. The pure compounds were obtained by re-crystallisation in acetone and water.General procedure: To acetophenone (1 mmol) catalyst STA (0.1 mmol or 10 mol %) was dissolved by stirring for 5-10 min. and further to this 4-chlorobenzaldehyde (1 mmol) was added and the mixture was magnetically stirred at room temperature until the completion of the reaction as confirmed by TLC. After the completion of the reaction the crude product was separated out, and then washed with water. The solid was filtered and dried. The crude product was further purified by recrystallization. All the products were characterised by their melting point, IR and 1H NMR and 13C NMR spectral analysis.General procedure: Chalcones (3a-j) were synthesized via Clasien-Schmidt condensation of substituted benzaldehyde and acetophenones. In dry DCM substituted benzaldehyde (1.0 mmol), acetophenone (1.0 mmol) in the presence of zirconium chloride (20 mol %) was taken. Reaction was stirred at room temperature for 2 h leading to generation of chalcone. Progress of reaction was monitored by TLC. After completion of reaction solvent was evaporated under the reduced pressure and residue was extracted with ethyl acetate and water. The organic layer was separated and dried over anhydrous Na2SO4 and filtered. The filtrate was evaporated under vacuum on a rotary evaporator.General procedure: A solution of the appropriate derivatives of both aldehyde (5mmol) and acetophenone (5mmol) in ethanol (15ml) was stirred until the both starting materials dissolved in room temperature. In a separate flask, NaOH (6mmol) was discolved to 15ml of an ethanol-water (1:1). The NaOH solution was then added dropwise to the mixture of aldehyde and acetophenone in room temperature. In most cases, after approxiamately 10 min the reaction mixture turned yellow and the crude products could be obtain as precipitates. The precipitates were washed by cold water, and air-dried overnight. The crude products were determined by TLC analysis and GC-MS. The reaction provided the chalcones in 70-85% yield.General procedure: Equimolar portions of the appropriately aromatic aldehydes (3 mmol, 1 equiv) and substituted acetophenone (3 mmol, 1 equiv) were dissolved in approximately 20 mL of ethanol. The mixture was allowed to stir for several minutes at 0 C to let dissolve. Than a 1 mL aliquot of a 40% aqueous potassium hydroxide solution was then slowly added dropwise to the reaction flask via a self-equalizing addition funnel. The reaction solution was allowed to stir at room temperature for approximately 4-6 h. Most commonly, a precipitate formed and was then collected by suction filtration.General procedure: To a stirred solution of acetophenone derivatives (1 mmol) and a benzlaldehyde derivatives (1 mmol) in EtOH (30 mL) was added 6 M KOH (4 mL) and the reaction mixture was stirred until the solids formed. The products were filtrated and washed carefully with ice water and cold EtOH; the resulting chalcones were purified by crystallization from EtOH in refrigerator. (Scheme 1)General procedure: Suitably substituted acetophenone (0.1 mol) and substituted aromatic aldehyde (0.1 mol) were dissolved in ethanol (30 mL). To the clear reaction mixture 10% NaOH was added drop wise. The reaction mixture was agitated and allowed to stand at room temperature for 24 h. The precipitated crystals of 1, 3-diaryl-2- propen-1-one were collected by filtration, washed and recrystallized from ethanol [36, 37].A mixture of equimolar quantities of 4-methoxybenzaldehyde and 4-chloroacetophenone were taken and stirred in ethanol (60 ml) and aqueous solution of NaOH (3%)was added drop by drop into mixture solution. After a particular drop, the whole solution turned out to be a precipitate. The obtained precipitate was filtered, dried and grained.General procedure: The reaction of 4-chloro/bromo acetophenone (1 mmol) (1, 2)was carried out with different substituted aryl aldehydes (1 mmol)in the presence of sodium hydroxide (30% soln., 10 ml). The resultingsolid product was filtered and recrystallized from chloroformwith 70-80% yield. The chalcones (1 mmol) so obtained were thencondensed with 2-hydrazinobenzothiazole-6-sulfonic acid amide(1.2 mmol) to synthesize 2-(3, 5-aryl-4, 5-dihydro-1H-pyrazol-1-yl)benzo[d]thiazole-6-sulfonamide (5a-h and 6a-f) by refluxinguntil reactants consumed. The solid compound so obtained was filteredand further purified by recrystallization from ethanol and theyield varies from 60-75%.General procedure: An aqueous solution of sodium hydroxide (20%, 5 mL) was slowly added to a stirred solution of ketones (1 mmol) and aldehydes (1 mmol) in ethanol (5 mL). The mixture was stirred at room temperature for 1 h and then poured into water (20 mL). The obtained solid was removed by filtration and washed with ice water and ethanol to nature. The crude product was purified by recrystallization from ethanol.General procedure: A mixture of aromatic aldehydes (0.01 mol) and acetophenone derivatives, namely acetophenone, 4-chloro-, 4-methyl-, 4-methoxyacetophenone, 3-acetylpridine, and/or 4-acetylpyridine (0.01 mol), was stirred in an ice bath for 1 h in 60 ml alcoholic sodium hydroxide 0.5M (1.2 g NaOH in 40 ml ethanol and 20 ml water)

Molecular Weight:272.72
XLogP3:3.7
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:272.0604073
Monoisotopic Mass:272.0604073
Topological Polar Surface Area:26.3
Heavy Atom Count:19
Complexity:311
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes