Gram-Scale Synthesis of Flavoring Ketones in One Pot via Alkylation-Decarboxylation on Benzylic Carbon Using a Commercial Solid Acid Catalyst.

ABSTRACT: The gram-scale synthesis of important flavoring ketones via alkylation of acetoacetic ester on substituted benzylic carbon followed by decarboxylation using a heterogeneous, commercial, solid acid catalyst is reported. The flavoring ketones were synthesized by the alkylation of acetoacetic ester, which proceeds through an S_N1-type reaction to generate an alkylated (β-ketoester) intermediate at the benzylic carbon, which is decarboxylated under the acidic condition. Among the solid acid catalysts used, Amberlyst-15 was found to be the best catalyst under the solvent-free condition. This protocol was successfully employed for the synthesis of various flavoring ketones such as raspberry ketone and ginger ketone with almost complete conversion and 82% isolated yield. The para-donati

SUBMITTER: Naikwadi DR 

PROVIDER: S-EPMC7315435 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature