Chemical Properties
3'-methoxypropiophenone is an organic compound belonging to the ketone class of compounds. It is a yellow to yellow brown liquid with a boiling point of 259 °C.
Uses
3'-methoxypropiophenone has a wide range of applications in the fields of medicine, chemistry, and industry.
Preparation
Preparation by reaction of ethylmagnesium bromide,
with m-methoxybenzonitrile (m.p. 60°)
with 3-methoxybenzaldehyde and oxidation of the resulting 1-(3-methoxyphenyl)-1-propanol with sodium dichromate in sulfuric acid (70%).
Synthesis
Under argon protection, 3,N-dimethoxy-N-methylbenzamide (5.86 g, 30.0 mmol) was dissolved in THF (150 mL) and cooled to 0°C. Slowly add ethylmagnesium bromide (0.960 mol/L THF solution, 100 mL, 96.0 mmol). After addition, bring to room temperature and stir for 3.5 hours. Upon completion of the reaction, the reaction was quenched with 1 mol/L hydrochloric acid and subsequently extracted with ethyl acetate. The organic layers were combined, washed sequentially with water and saturated saline, and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded m-methoxypropiophenone (4.93 g, 30.0 mmol, quantitative yield) as a yellow oil.1H-NMR (400 MHz, CDCl3): δ 1.23 (3H, t, J = 7.3 Hz), 3.00 (2H, q, J = 7.3 Hz), 3.86 (3H, s), 7.10 (1H, dd, J = 7.9 , 2.4 Hz), 7.37 (1H, t, J = 7.9 Hz), 7.50 (1H, t, J = 2.4 Hz), 7.54 (1H, d, J = 7.9 Hz).
References
[1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 375 - 381
[2] Patent: WO2007/62190, 2007, A2. Location in patent: Page/Page column 29; 30
[3] Patent: WO2007/62145, 2007, A2. Location in patent: Page/Page column 41
[4] Patent: WO2007/44796, 2007, A2. Location in patent: Page/Page column 35-36
[5] Angewandte Chemie - International Edition, 2016, vol. 55, # 52, p. 16115 - 16118
