ChemicalBook CAS DataBase List 3'-methoxypropiophenone

3'-methoxypropiophenone synthesis

12synthesis methods

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

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%).

925-90-6 Synthesis

925-90-6
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$12.00/5ml

152121-82-9 Synthesis

152121-82-9
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37951-49-8
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$60.00/50mg

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