3-Methoxyacetophenone

5,5'-Dimethyl-2,2'-Bipyridine 8 (4.10 mg, 0.023 mmol, 15 mol%), MgCl2 (28.4 mg, 0.300 mmol, 200 mol%), Ni(acac)2 (5.90 mg, 0.023 mmol, 15 mol%), and zinc powder (29.4 mg, 0.450 mmol, 300 mol%) were placed into a flame-dried Schlenk tube equipped with a magnetic stir bar. The tube was then transferred to a dry glove box, and TBAI (27.7 mg, 0.075 mmol, 50 mol%) was added. The tube was covered with a rubber diaphragm and then removed from the glove box.

Then, acidic chloride (0.225 mmol, 150 mol%), methanesulfonate (0.150 mmol, 100 mol%), THF (0.8 mL), and CH3CN (0.2 mL) were added via syringe. The reaction mixture was stirred for 12 hours at 30°C under a N2 atmosphere and then directly loaded onto a silica gel column without further treatment. The reaction vessel was rinsed with a small amount of DCM to remove any residue. Rapid column chromatography (SiO2: ethyl acetate in hexane) was performed. 1-(3-methoxyphenyl)acetone (38). 21 was prepared using 3-methoxybenzoyl chloride (0.225 mmol, 150 mol%) and methanesulfonate (0.150 mmol, 100 mol%). After purification by column chromatography (SiO2: 10% ethyl acetate in hexane), a colorless oily 3-methoxyacetophenone (10.8 mg, 48% yield) was obtained.

clear slightly yellow to slightly brown liquid

It is applied in the asymmetric transfer hydrogenation of ketones catalyzed by ruthenium(II) complexes.

Journal of the American Chemical Society, 109, p. 7137, 1987 DOI: 10.1021/ja00257a038
Synthesis, p. 406, 1987 DOI: 10.1055/s-1987-27965

Non flammable