3-(2,4-Dichlorophenyl)-2-propenoic acid

General procedure: To a 5 mL round bottom flask equipped with a stirbar, trans-2’-hydroxychalcone 1a (1 mmol), K2CO3(1.38 g, 10 mmol), 35percent H2O2 solution (0.5 mL) and2 mL acetonitrile were added. The reaction was stirredat room temperature and monitored by TLC (thin layerchromatograph) until disappearance of the starting material.The solvent was evaporated with reduced pressure. To theresidue, it was added 1 mol L-1 hydrochloric acid, the solidwas filtered to afford 2a as white solid (133 mg, 90percent);1H NMR (300 MHz, DMSO-d6) d 7.58 (d, 1H, J 16 Hz), 7.42-7.69 (m, 5H), 6.53 (d, 1H, J 16 Hz); 13C NMR(300 MHz, DMSO-d6) d 167.7, 144.0, 134.3, 130.3, 128.9, 128.2, 119.3.General procedure: The suitable aldehyde (10 mmol), malonic acid (30 mmol, 3.12 g) and piperidine (0.5 mL) were dissolved in pyridine (20 mL) and the mixture was heated under reflux for 4 h. The solution was cooled to room temperature and poured in ice-cold aqueous HCl (100 mL, 3 M). The white solid precipitate was filtered, washed with water (350 mL), aqueous NaHCO3 (20 mL, 5percent w/v), then again with water (250 mL) and dried in an oven (60 C). If required, the crude solid was recrystallysed from EtOH/H2O.General procedure: According to method II [23] [4a, 5a, 7a, 8a, 14a, 15a, 16a, 17a]:15 mmols of cinnamic acid were dissolved in 45 ml of dried toluene.Next, 15 mmols of DBU were added to the mixture and stirred inroom temperature for 1 h. After that time 15 mmols of iodomethanewere added and stirring was continued for at least 20 h.Then, 20 ml of toluene was added and mixture was washed twicewith 70 ml of 0.5% NaOH and 70 ml of water. Organic layer wasdried with anhydrous sodium sulfate. Finally, the solvent wasevaporated.

Molecular Weight:217.05
XLogP3:3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:215.9744848
Monoisotopic Mass:215.9744848
Topological Polar Surface Area:37.3
Heavy Atom Count:13
Complexity:216
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes