(±)-acetyl(4-methoxyphenyl)acetonitrile synthesis

Yield:63895-78-3 95%

Reaction Conditions:

with sodiumReflux;

Steps:

59.1

Step 1. 2-(4-Methoxyphenyl)-3-oxobutanenitrile Into a 500-mL 3-necked round-bottom flask, was placed a solution of 2-(4-methoxyphenyl)acetonitrile (20 g, 136 mmol, 1.00 equiv) in ethyl acetate (400 mL). To the above was added sodium (3.8 g, 165 mmol, 1.21 equiv) in several batches. The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at reflux. The resulting mixture was filtered, and the solids were dissolved in 400 mL of H₂O. The resulting solution was extracted with 2*100 mL of ether and the aqueous layers combined, acidified with AcOH, and extracted with ethyl acetate (200 mL*3). The ethyl acetate layers were washed with Sat. NaHCO₃, dried over Na₂SO₄., and concentrated to get 24.7 g (95%) of 2-(4-methoxyphenyl)-3-oxobutanenitrile as a white solid.

References:

US2012/277224,2012,A1 Location in patent:Page/Page column 73