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%.

Synthesis and biological and structural characterization of ...

[Journal of Medicinal Chemistry, , vol. 46, # 8 p. 1306 - 1317]

Claisen Condensation as a Facile Route to an α-Alkoxy-cinnam...

[Organic Process Research and Development, , vol. 8, # 6 p. 838 - 845]

Process development on the enantioselective enzymatic hydrol...

[Deussen, Heinz-Josef; Zundel, Magali; Valdois, Marine; Lehmann, Soren Vig; Weil, Volker; Mailand Hjort, Carsten; stergaard, Peter Rahbek; Marcussen, Erik; Ebdrup, Soren Organic Process Research and Development, 2003 , vol. 7, # 1 p. 82 - 88]