Issue 10, 1994

Selective mono-methylation of arylacetonitriles and methyl arylacetates by dimethyl carbonate

Abstract

Both arylacetonitriles and methyl arylacetates react with dimethyl carbonate (DMC)(20 molar excess) at 180–200 °C in the presence of K2CO3 to produce monomethylated 2-arylpropionitriles and methyl 2-arylpropionates, respectively, with a selectivity >99.5%. The reaction, with wide application, proceeds by DMC acting as a methoxycarbonylating agent towards the ArCHX anion (X = CN, CO2Me) and as a methylating agent to ArC(CO2Me)X. DMC also proved to be the best solvent for such reactions.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1994, 1323-1328

Selective mono-methylation of arylacetonitriles and methyl arylacetates by dimethyl carbonate

M. Selva, C. A. Marques and P. Tundo, J. Chem. Soc., Perkin Trans. 1, 1994, 1323 DOI: 10.1039/P19940001323

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