
3'-methoxypropiophenone synthesis
- Product Name:3'-methoxypropiophenone
- CAS Number:37951-49-8
- Molecular formula:C10H12O2
- Molecular Weight:164.2
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%).

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Yield:37951-49-8 100%
Reaction Conditions:
Stage #1: ethylmagnesium bromide;N,3‐dimethoxy‐N‐methylbenzamide in tetrahydrofuran at 0 - 20; for 3.5 h;Inert atmosphere;
Stage #2: with hydrogenchloride in tetrahydrofuran;water;Inert atmosphere;
Steps:
To a stirredsolution of 14 (5.86 g, 30.0 mmol) in THF (150 mL) was slowly added EtMgBr (0.960 mol/L in THF, 100 mL, 96.0 mmol)at 0 oC under argon atmosphere. After stirring for 3.5 h at roomtemperature, the reaction was quenched with 1 mol/L HCland the resulting mixture was extracted with EtOAc. The organic layer was washed with water followed by brine, dried over Na2SO4, and concentrated in vacuo to give the title compound (4.93 g, 30.0 mmol, quant.) 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:
Ochiai, Koji;Takita, Satoshi;Kojima, Akihiko;Eiraku, Tomohiko;Iwase, Kazuhiko;Kishi, Tetsuya;Ohinata, Akira;Yageta, Yuichi;Yasue, Tokutaro;Adams, David R.;Kohno, Yasushi [Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,# 1,p. 375 - 381] Location in patent:supporting information

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