Claisen Condensation as a Facile Route to an α-Alkoxy-cinnamate: Synthesis of Ethyl (2 S)-2-Ethoxy-3-(4-hydroxyphenyl) propanoate

MT Linderberg, M Moge…

Index: Linderberg, Mats T.; Moge, Mikael; Sivadasan, Sivaprasad Organic Process Research and Development, 2004 , vol. 8, # 6 p. 838 - 845

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Citation Number: 24

Abstract

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%.

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