Claisen condensation as a facile route to an α-alkoxy-cinnamate:: Synthesis of ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate

The title compound was prepared from p-anisaldehyde and ethyl ethoxyacetate via a racemic synthetic route: The synthesis involves a Claisen-type condensation in which the elimination was unexpectedly promoted by an excess of the ester. The process has been successfully performed on a 2000-L scale with a total yield over seven steps of 19%.