Selective mono-methylation of arylacetonitriles and methyl arylacetates by dimethyl carbonate
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 1323-1328
- https://doi.org/10.1039/p19940001323
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 ArCH–X anion (X = CN, CO2Me) and as a methylating agent to ArC–(CO2Me)X. DMC also proved to be the best solvent for such reactions.Keywords
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