ChemicalBook CAS DataBase List (S)-(+)-2-Phenylpropionic acid

(S)-(+)-2-Phenylpropionic acid synthesis

5synthesis methods

Product Name:(S)-(+)-2-Phenylpropionic acid
CAS Number:7782-24-3
Molecular formula:C9H10O2
Molecular Weight:150.17

93-53-8 Synthesis

93-53-8
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$11.00/5g

7782-24-3
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$28.00/1G

Yield:7782-24-3 79%

Reaction Conditions:

with sodium chlorite;sodium dihydrogenphosphate dihydrate;2-methyl-but-2-ene in water;tert-butyl alcohol at 0 - 20; for 2 h;

Steps:

4.4 (S)-2-Phenylpropanoic acid 3
Aldehyde 8 (1.35 g, 10.1 mmol) was dissolved in mixture of t-BuOH and 2-methyl-2-butene (6 mL in 2:1 ratio). To it NaClO₂ (1.81 g, 20.1 mmol) and NaH₂PO₄·2H₂O (3.12 g, 20.1 mmol) dissolved in minimum amount of water were added to reaction mixture at 0 °C and allowed to stir for 2 h at room temperature. Solvent was removed under reduced pressure and extracted with EtOAc (2×10.0 mL), washed with water (10.0 mL) and brine (10.0 mL). The combined organic layers were dried (Na₂SO₄), concentrated in vacuo, and purified by column chromatography (silica gel, 60-120 mesh, R_f 0.30, 10% EtOAc/hexane) to afford 3 (1.20 g, 79%) as a yellow oil. Found: C, 71.72; H, 6.45. C₉H₁₀O₂ requires C, 71.98; H, 6.71%; [α]_D²⁵ +72.7 (c 0.4, CHCl₃); IR (neat) νˉνˉ: 3443, 3012, 2977, 1745, 746 cm^-1; ¹H NMR (CDCl₃, 500 MHz): 7.33-7.18 (5H, m, Ar-H), 3.70 (1H, q, J=7.2 Hz, -CHCOOH), 1.52 (3H, d, J=7.2 Hz, -CH₃); ¹³C NMR (CDCl₃, 75 MHz): 176.0, 132.2, 129.8, 129.0, 128.8, 49.7, 17.5; MS (ESI) m/z 173 [M+Na]⁺.

References:

Krishna, Palakodety Radha;Arun Kumar, Pendyala Venkata;Mallula, Venkata Satyanarayana;Ramakrishna, Kallaganti V.S. [Tetrahedron,2013,vol. 69,# 10,p. 2319 - 2326]

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