2-(3-CHLOROPHENYL)PROPIONIC ACID

Methyl 2-(3-ehlorophenyi)propanoate (590 ig. 2.97 mmol) in THF (12 ml .) and MeOH (1 mL) at T was treated with 2N NaOH (aq) (4.2 mL. 8.41 mmol) and stirred overnight. The reaction mixture was concentrated in vacuo and the resulting aqueous layer was acidified with IN HCl to pH 1 and extracted with EtOAc. The combined organic fractions were washed with brine, dried (MgS04) and concentrated in vacuo. The residue was purified on silica (40 g 0-30% EtOAc in cyclohexane) to give the title compound as a pale yellow oil (229 mg, 42%). NMR (400 MHz, CDCI3): e5 7.34-7.15 (411, m), 3.72 (III, q, J = 7.3 Hz), 1.51 (311, d, J = 7.3 Hz).Preparation of 2-(3-chlorophenyl) propanoic acid Methyl-2-(3-chlorophenyl) propanoate (10 g), ethanol (50 ml) and sodium hydroxide (2.0 g) were charged into a round bottom flask and heated to reflux till substantial completion of the reaction. The reaction mass was distilled under reduced pressure and water (50 mL) was charged to the distilled mass. The pH was adjusted to 1-2 with 20% aqueous HCl (10 ml). Ethyl acetate (50 mL) was charged and stirred at 28 C. The aqueous and organic layers were separated. The aqueous layer was extracted with ethyl acetate (50 ml). The combined organic layer was washed with water (30 mL). The organic layer was distilled under reduced pressure at 60 C. to afford the title compound. Yield: 9.1 g

Molecular Weight:184.62
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:184.0291072
Monoisotopic Mass:184.0291072
Topological Polar Surface Area:37.3
Heavy Atom Count:12
Complexity:170
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes