Application of 13338-63-1,Some common heterocyclic compound, 13338-63-1, name is 3,4,5-Trimethoxyphenylacetonitrile, molecular formula is C11H13NO3, 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.
Step 1 Preparation of (Z)-3-(3-nitro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile 3.0 g of 3-nitro-4-methoxybenzaldehyde, 3.4 g of 3,4,5-trimethoxyphenylacetonitrile, 800 mg of sodium hydroxide and 100 mg of octylmethylammonium chloride were dissolved in 15 ml of water and 15 ml of dichloromethane and reacted for 4 hours at room temperature. Ice water was added to the reaction liquid, which was then extracted three times each with dichloromethane. The extract was dried with anhydrous sodium sulfate and concentrated. The concentrated liquid was purified by crystallization (ethyl acetate) to obtain 4.4 g of the intended compound. The yield was 72%. 1 H-NMR(CDCl3): 8.30 (1H, dd, J=2.4, J=9.0), 8.21 (1H, d, J=2.4), 7.38 (1H, s), 7.21 (1H, d, J=9.0), 6.86 (2H, s), 4.05 (3H, s), 3.94 (6H, s), 3.89 (3H, s); mass spectrum (m/z): 370 (M+); melting point 191-192 C.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4,5-Trimethoxyphenylacetonitrile, its application will become more common.
Reference:
Patent; Ajinomoto Co., Ltd.; US5525632; (1996); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts