3-(4-Methoxyphenyl)propionic acid

White tolight beige crystalline powder

To a solution of 3-(4-methoxyphenyl)acrylic acid (15, 14.7 mmol) in THF (50 mL) was added a catalytic amount of 10percent palladium on activated carbon to carry out hydrogenation, followed by stirring for 5 h at room temperature. The mixture was filtered, and the filtrate was concentrated in vacuo to give a white solid with a yield of 95.2percent, mp 102-103 °CPlus p-methoxycinnamic acid(11a, 14.7 mmol), tetrahydrofuran (50 mL), Methanol (20 mL), Catalytic amount of 10percent Pd / C, hydrogen, The reaction was stirred at room temperature for 5 h. The reaction was terminated and the solid was filtered off. The solution was concentrated to dryness under reduced pressure to give a white solid, 95.2percent yield, General procedure: A mixture of zinc powder (25 g, 0.384 mol) and mercuric chloride(3.1 g, 0.0114 mol) was suspended in 100 mL of water in a 250 mLbeaker. The mixture was treated with 50 mL of con. HCl slowly dropwise and after completion of addition, the stirring was continued for15 min. The mixture was decanted to separate the solution and theremaining Zn-Hg amalgam was used for reduction. To a mixture of substituted cinnamic acid (1a-e, 0.134 mol), THF(150 mL) and 5 N HCl (100 mL) was added above freshly prepared Zn-Hg amalgam slowly portion wise. An additional 5 N HCl (50 mL) addedand the stirring continued for 2 h. After completion of reaction, asmonitored by TLC hexane/ethyl acetate (8:2), the reaction mixture waspoured into water (200 mL) and extracted with chloroform(2×400 mL), The organic layer was washed with brine solution, driedover Na2SO4 and concentrated. The crude residue was subjected to column chromatography on silica gel using hexane/ethyl acetate mixturesas eluents. The fractions were monitored using TLC and purecompound was obtained from the fractions eluted with ethyl acetate inhexane, 5percent/95percent (v/v). These fractions were combined and concentratedto obtained 3-(substituted-phenyl)-propionic acids (2a-e) asoily compounds with yields of 79–86percent.

Used as pharmaceutical intermediate

Molecular Weight:180.20
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:180.078644241
Monoisotopic Mass:180.078644241
Topological Polar Surface Area:46.5
Heavy Atom Count:13
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes