SELECTIVE MONO-METHYLATION OF ARYLACETONITRILES AND METHYL ARYLACETATES BY DIMETHYL CARBONATE

Authors
SELVA M MARQUES CA TUNDO P
Citation
M. Selva et al., SELECTIVE MONO-METHYLATION OF ARYLACETONITRILES AND METHYL ARYLACETATES BY DIMETHYL CARBONATE, Journal of the Chemical Society. Perkin transactions. I, (10), 1994, pp. 1323-1328
Citations number
44
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
10
Year of publication
1994
Pages
1323 - 1328
Database
ISI
SICI code
0300-922X(1994):10<1323:SMOAAM>2.0.ZU;2-U
Abstract
Both arylacetonitriles and methyl arylacetates react with dimethyl car bonate (DMC) (20 molar excess) at 180-200 degrees C in the presence of K2CO3 to produce monomethylated 2-arylpropionitriles and methyl 2-ary lpropionates, respectively, with a selectivity >99.5%. The reaction, w ith wide application, proceeds by DMC acting as a meth oxycarbonylatin g agent towards the ArCH(-)X anion (X = CN, CO(2)Me) and as a methylat ing agent to ArC-(CO(2)Me)X. DMC also proved to be the best solvent fo r such reactions.