ChemicalBook CAS DataBase List ETHYL 2-PHENYLPROPIONATE

ETHYL 2-PHENYLPROPIONATE synthesis

8synthesis methods

Product Name:ETHYL 2-PHENYLPROPIONATE
CAS Number:2510-99-8
Molecular formula:C11H14O2
Molecular Weight:178.23

101-97-3 Synthesis

101-97-3
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2510-99-8
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Yield: 85%

Reaction Conditions:

Stage #1:Ethyl 2-phenylethanoate with diisopropylamine in tetrahydrofuran;n-heptane at 40; for 1.5 h;
Stage #2:methyl iodide with 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone in tetrahydrofuran;n-heptane at 20;

Steps:

5.1.19
Under N₂ atmosphere, a solution of ethyl phenylacetate (50.0 g, 0.304 mol) in anhydrous THF (300 mL) was cooled to -40°αC and a solution of LDA (2.0 M in heptane, 152 mL, 304 mmol) was added dropwise over 30 min. The reaction mixture was stirred for 1 h, and MeI (60.51 g, 0.426 mmol) was added dropwise, followed by the addition of DMPU (20 mL). After 1 h, the reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured into H₂O (400 mL) and extracted with EtOAc (3*100 mL). The combined organic layers were washed with saturated aqueous NH₄Cl (100 mL), aqueous HCl (1 M, 100 mL), saturated aqueous NaHCO₃ (100 mL), and brine (100 mL), dried (MgSO₄) and evaporated in vacuo. The residue was distilled in high vacuo to give 2-phenyl-propionic acid ethyl ester (46.13 g, 85%) as an oil. ¹H NMR (CDCl₃): δ=7.36-7.18 (m, 5H), 4.11 (m, 2H), 3.69 (q, J=7.1, 1H), 1.49 (d, J=7.1, 3H), 1.19 (t, J=7.1, 3H). ¹³C NMR (CDCl₃): δ=174.7, 140.9, 128.8 (2*), 127.6 (2*), 127.2, 60.9, 45.7, 18.8, 14.3.

References:

Dasseux, Jean-Louis Henri;Oniciu, Carmen Daniela US2005/192347, 2005, A1 Location in patent:Page/Page column 75