3-(3-Chlorophenyl)-2-propenoic acid

white crystalline powder or crystals

General procedure: To a stirred solution of 6.76 g (65 mmol) malonic acid in pyridine (5 mL) and piperidine (0.5 mL), the corresponding aldehyde (50 mmol) was added slowly under 85 General procedure: A 100 mL, round-bottomed flask was charged with Na2B4O7 ·10H2O (5 mmol, 1.9 g) and heated at 160-180°C for 3-4 h untilconstant weight. Benzyl-triethylammonium chloride (5 mmol, 1.14 g), DMAP (5 mmol, 0.61 g), Py (20 mmol, 1.61 mL) andNMP (3 mL) were added. This mixture was heated at reflux, under stirring for 2-2.5 h, when benzyltriethylammonium-sodiumtetraborate complex resulted in situ. The solution temperature wasdecreased to 70°C and acetic acid (50 mmol, 2.85 mL), andp-chlorobenzaldehyde (5 mmol, 0.70 g) were added. A condenserwas fitted to the flask and the excess of acetic acid was removedby distillation until the temperature in the flask reached 185-187°C. The obtained solution was finally heated under reflux at185-190°C for 6-10 h (see Table 1). After cooling down, thesolution was treated with water (5-7 mL) and aqueous NaOH(20percent) to pH=9-10, and the unreacted aromatic aldehyde wasdistilled as azeotropic mixture with water, until the distillate wasclear. The final solution was filtered off and the filtrate was treatedwith HCl solution 15-20percent until pH=1-2, under cooling on ice andstirring for 2-3 h, when cinnamic acid precipitated. The resultedproduct was filtered off, washed with cold water (15-20 mL) anddried in a vacuum oven. Recrystallization from aqueous EtOH orEtOAc:petroleum ether gave pure products as white or yellowishcrystals. In all cases, a good trans-selectivity for the cinnamicacids was observed.

Used in organic synthesis, it is the raw material for the production of 5-chloroindanone, and also the intermediate of medicine and pesticide

Molecular Weight:182.60
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:182.0134572
Monoisotopic Mass:182.0134572
Topological Polar Surface Area:37.3
Heavy Atom Count:12
Complexity:189
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes