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. Recommanded Product: 69395-13-7
To a solution of 4- (2- hydroxyethyl) benzonitrile (120 mg, 0.816 mmol) in acetone (3 ML), Jone’s reagent (1. 5ML, 4.005 mmol) was added.. After stirring for 10 minutes at room temperature, the crude reaction mixture was poured into water (10 ML) and extracted with CHC13 (6 x 10 mL). Combined organics were dried over magnesium sulfate, filtered, and concentrated to give (4-cyanophenyl- acetic acid which was used without purification. To a solution of (4-cyanophenyl) acetic acid (131 MG, 0.816 mmol) in ETOH (0.5 ML) at 0C was bubbled HCl (g) until saturation. Reaction mixture was allowed to warm to room temperature slowly. After overnight stirring, the crude reaction mixture was concentrated in vacuo. This residue was taken up in ETOH (4 ML) and ethylene diamine (0.1 mL, 1.49 mmol) was added. After stirring at room temperature for two hours, the crude reaction mixture was concentrated under reduced pressure and then re-dissolved in DMF (2 mL). To this solution was added 1M NAOH (2 mL, 2 mmol) and the reaction stirred at room temperature for three hours. Crude reaction mixture was neutralized with 1M HC1 to a pH 6 and extracted with CHC13 (4 x 15 ML). Product was found in the water layer, so combined all layers and concentrated in vacuo, re-dissolved in CHCL3/MEOH, and filtered to remove precipitate. Concentration of the filtrate gives [4- (4, 5-dihydro-lH-imidazol-2-yl) phenyl] acetic acid, which was used without further purification. LCMS (ES) 205.1 771/Z (M +H) +
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 69395-13-7, its application will become more common.
Reference:
Patent; MERCK & CO., INC.; WO2004/54584; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts