![2510-99-8](/CAS/GIF/2510-99-8.gif)
ETHYL 2-PHENYLPROPIONATE synthesis
- Product Name:ETHYL 2-PHENYLPROPIONATE
- CAS Number:2510-99-8
- Molecular formula:C11H14O2
- Molecular Weight:178.23
![Ethyl phenylacetate](/CAS/GIF/101-97-3.gif)
101-97-3
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![ETHYL 2-PHENYLPROPIONATE](/CAS/GIF/2510-99-8.gif)
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
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![ETHYL 2-PHENYLPROPIONATE](/CAS/GIF/2510-99-8.gif)
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