Some common heterocyclic compound, 103-25-3, name is Methyl 3-phenylpropionate, molecular formula is C10H12O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C10H12O2
General procedure: A mixture of Lithium aluminum hydride (9.5 g, 0.250 mol), dry THF(250 mL), to it add substituted dihydrocinnamic acid methyl ester (3ae,0.127 mol), in THF (50 mL) was added slowly drop wise during30 min. After completion of addition the reaction mixture was stirredfor 2 h at rt, after completion of reaction as monitored by TLC hexane/ethyl acetate (8:2), the reaction mixture was poured in water (200 mL),acidified with 5 N HCl, extract with chloroform (2¡Á400 mL), extractwas wash with water, brine solution, dried over Na2SO4 and concentrated.The crude residue was subjected to column chromatographyon silica gel, column was eluted with hexane/ethyl acetate mixtures,pure compound was eluted in ethyl acetate in hexane, 10%/90% (v/v)which was monitored by TLC, pure fractions were combined and concentratedto obtained 3-(substituted phenyl)- propan-1-ol as oily compoundswith yields of 73-77%. 3.2.13 3-(Phenyl)-propan-1-ol (4a) Weight: 9.10?g; % yield: 73.2%; 1H NMR (CDCl3, 400?MHz): delta 7.32-7.28 (2H, m, H-3′, 5′), 7.14 (2H, d, J?=?8.0?Hz, H-2′, 6′), 7.06 (1H, t, J?=?7.2?Hz, H-4′), 3.56 (2H, t, J?=?8.0?Hz, CH2), 2.56 (2H, t, J?=?7.2?Hz, H-3), 2.43 (1H, s, OH), 1.86 (2H, quin, J?=?7.6?Hz, H-2); 13C NMR (CDCl3, 100?MHz): delta 146.2 (C-1′), 132.8 (C-3′, 5′), 130.2 (C-2′, 6′), 126.8 (C-4′), 65.8 (C-1), 38.3 (C-2), 31.9 (C-3); LC-MS: m/z 135.2 (M?-?H)-.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 103-25-3, its application will become more common.
Reference:
Article; Meka, Bharani; Ravada, Suryachandra Rao; Muthyala, Murali Krishna Kumar; Kurre, Purna Nagasree; Golakoti, Trimurtulu; Bioorganic Chemistry; vol. 80; (2018); p. 408 – 421;,
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