Hydrochloric Acid → HCID 5052107, compound

Temperature

-78 °C

27.1 ml (67.8 mmol) of a 2.5 M solution of n-butyllithium in hexane is added drop by drop at −78° C. under argon to a solution of 4.4 g (108.6 mmol) of acetonitrile in 50 ml of anhydrous tetrahydrofuran. The reaction mixture is stirred for 30 min at −78° C., then a solution of 5.2 g (27.15 mmol) of ethyl 4-ethoxybenzoate diluted in 30 ml of tetrahydrofuran is added at −78° C. drop by drop to the reaction mixture. The reaction mixture is stirred for 2 h at −78° C., then 1 M hydrochloric acid solution is added, and the product is extracted several times with ethyl acetate. The organic phases are combined, dried on magnesium sulfate and concentrated. The solid is triturated in 15 ml of methanol to yield 4.4 g (80%) of 4-ethoxyphenyl-3-oxopropanenitrile in the form of a white solid.

1. additionis added at −78° C. drop by drop to the reaction mixture
2. stirringThe reaction mixture is stirred for 2 h at −78° C.
3. extractionthe product is extracted several times with ethyl acetate
4. customdried on magnesium sulfate
5. concentrationconcentrated
6. customThe solid is triturated in 15 ml of methanol

ORD record

ord-6573f80fabca4686b2bfca7b07f94978

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085575B2