METHYL 3-(4-(BENZYLOXY)PHENYL)PROPANOATE Chemical Properties

storage temp. 

Sealed in dry,Room Temperature

METHYL 3-(4-(BENZYLOXY)PHENYL)PROPANOATE Usage And Synthesis

Synthesis

Procedure for the synthesis of methyl 3-(4-(benzyloxy)phenyl)propionate: in 40 mL of acetonitrile, methyl 3-(4-hydroxyphenyl)propionate (1.54 g, 8.55 mmol), potassium carbonate (3.55 g, 25.64 mmol) and benzyl bromide (4.39 g, 25.64 mmol) were mixed to form a suspension. The reaction mixture was heated to reflux for 1 hour. Upon completion of the reaction, the mixture was poured into 120 mL of water and the pH was adjusted to 2 with 10% aqueous hydrochloric acid, followed by extraction with ethyl acetate (2 x 100 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography with 0→5% ethyl acetate/hexane as eluent to give methyl 3-(4-(benzyloxy)phenyl)propionate (2.01 g, white solid, 88% yield).1H NMR (CDCl3, 250 MHz) δ ppm: 7.51-7.29 (m, 5H), 7.14 (d, J = 8.8 Hz, 2H). 6.92 (d, J = 8.8 Hz, 2H), 5.05 (s, 2H), 3.69 (s, 3H), 2.92 (t, J = 7.6 Hz, 2H), 2.62 (t, J = 7.6 Hz, 2H).

References

[1] Patent: US2002/65246, 2002, A1
[2] Patent: US6414179, 2002, B1
[3] Patent: WO2010/70076, 2010, A1. Location in patent: Page/Page column 104
[4] Patent: EP2952517, 2015, A1. Location in patent: Paragraph 0217
[5] Bulletin of the Polish Academy of Sciences, Chemistry, 1986, vol. 34, # 3-4, p. 115 - 122

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