Electric Literature of 69395-13-7,Some common heterocyclic compound, 69395-13-7, name is 4-(2-Hydroxyethyl)benzonitrile, molecular formula is C9H9NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
PREPARATION 13 Preparation of 4-carbamoylphenethyl bromide and 4-cyanophenethyl bromide STR36 A solution of phosphorus tribromide (5 g) in carbon tetrachloride (10 ml) was added, dropwise, to a solution of 4-cyanophenethyl alcohol (8.06 g) in carbon tetrachloride (60 ml). The mixture was heated under reflux for 4 hours. On cooling to room temperature, the mixture was poured onto ice (200 g). The layers were separated and the organic layer was washed with 10% aqueous sodium carbonate (50 ml) and brine (50 ml), dried (MgSO4) and concentrated in vacuo to give a colourless oil which solidified on standing. The solid was chromatographed on silica eluding with ethyl acetate containing hexane (20%). The fractions containing the less polar (higher Rf) product were combined and concentrated in vacuo to give 4-cyanophenethyl bromide as a yellow oil which solidified on standing, yield 8.9 g. The fractions containing the more polar (lower Rf) product were combined and concentrated in vacuo to give 4-carbamoylphenethyl bromide as a colourless solid, yield 0.47 g, m.p. 152-153.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(2-Hydroxyethyl)benzonitrile, its application will become more common.
Reference:
Patent; Pfizer Inc.; US5340831; (1994); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts