Scientists from the Zelinsky Institute conducted a detailed study of the Meyer reaction

Arylnitromethanes are valuable intermediates in fine organic synthesis used to obtain various aromatic and heteroaromatic compounds. For almost 150 years, the Meyer reaction, which involves the reaction of an alkyl halide with silver nitrite, has been most commonly used to produce aryl nitromethanes. However, for a long time it was considered that this process was not applicable for the synthesis of arylnitromethanes containing electron-donating substituents in the aromatic ring, due to the predominant formation of nitrous acid esters as products.

Scientists of the Laboratory of Medical Chemistry of ZIOC conducted a detailed study of the Meyer reaction, the range of compatible and unsuitable substrates for it. It wa shown that polymethoxy-substituted benzyl chlorides reacted with AgNO2 to form arylnitromethanes and the corresponding nitrite esters in an average ratio of 40:60. One of the key features of the study is the modification of the method for isolating the obtained compounds. At the end of the process, the product mixture reacts with urea in methanol, which allows the resulting nitrite ester to be converted into benzyl alcohol, and arylnitromethane to be isolated without loss. The liberated benzyl alcohol can be transformed to the corresponding chloride and re-introduced into the Meyer reaction.

Source:

Anna S. Maksimenko, Petr A. Buikin, Elena D. Daeva, Victor P. Kislyi, Victor V. Semenov Preparation of Ring-Methoxylated Arylnitromethanes by the Victor Meyer Reaction. Synthesis 2022, 54, 2724-2730. DOI: 10.1055/s-0041-1737534.