Introduction of a new synthetic route about 3,5-Dimethoxybenzonitrile

According to the analysis of related databases, 19179-31-8, the application of this compound in the production field has become more and more popular.

19179-31-8, Adding a certain compound to certain chemical reactions, such as: 19179-31-8, name is 3,5-Dimethoxybenzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 19179-31-8.

Compound 5:1-(3,5-Dimethoxy-phenyl)-pentan-1-one To Mg turnings (1.12 g, 46.7 mmol), dried in an oven for 1 hour, and dry THF (32 ml) was added 1-butylbromide (4.46 g, 32.5 mmol) and allowed to react at reflux for half an hour. After formation of the Grignard, 3,5-dimethoxybenzonitrile (4 g, 24.5 mmol) was added and the mixture was refluxed for 4 h. The reaction was cooled with ice for 15 minutes followed by the slow addition of 40 ml of 6N HCl and then the mixture was refluxed for 16 h. The THF was removed and the residue dissolved in EtOAc (60 ml) and 6N HCl (15 ml). The layers were separated, the aqueous layer extracted with EtOAc (4*20 ml). The combined EtOAc extracts were extracted and washed with saturated NaHCO3, water and brine. After drying the organic phase was concentrated and the residue resolved on silica gel eluding with EtOAc/hexanes (5:25), to yield 3.52 g (64.7%) of compound 5 as a white solid. Rf=0.43 (Hexane:ethyl acetate 9:1); IR (KBr pellet) 2956, 1601, 1206, 1067, 755 cm-1; 1H NMR delta 7.09 (d, J=2.31 Hz, 2H), 6.64 (t, J=2.31 Hz, 1H), 3.84 (s, 6H), 2.92 (t, J=7.4 Hz, 2H), 1.71 (q, J=7.71 Hz, 2H), 1.40 (s, J=7.71 Hz, 2H), 0.95 (t, J=7.32 Hz, 3H); 13C NMR delta 200.51, 161.10, 139.33, 106.17, 105.29, 55.83, 38.70, 26.84, 22.71, 14.17; MS: (ESI, Pos.) m/z 245 ([M+23]+).

According to the analysis of related databases, 19179-31-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Moore II, Bob M.; Ferreira, Antonio M.; Krishnamurthy, Mathangi; US2004/242593; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts