Menshutkin reaction

The Menshutkin reaction in organic chemistry converts a tertiary amine to a quaternary ammonium salt by reaction with an alkyl halide:



The reaction between amines and alkyl halogenides is hard to control, making alternative routes (for instance reductive amination) more attractive. However, when quaternary ammonium salts are the desired end product, this reaction becomes an interesting option. Yields are good and the reaction is easily performed. R1-R4 can but don't have to be identical. Some phase transfer catalysts (PTC) can be prepared according to the Menshutkin reaction, for instance the synthesis of triethyl benzyl ammonium chloride (TEBA) from triethylamine and benzyl chloride:



The reaction has been named after its discoverer, the Russian chemist Nikolaj Menšutkin, who described the procedure in 1890. Depending on the source, his name (and the reaction named after him) is spelled as Menšutkin, Menshutkin or Menschutkin.