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%.