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Article Dans Une Revue Beilstein Journal of Organic Chemistry Année : 2019

Efficient synthesis of 4-substituted- ortho -phthalaldehyde analogues: toward the emergence of new building blocks

Résumé

4-Methoxy-ortho-phthalaldehyde and 4-hydroxy-ortho-phthalaldehyde are potentially useful molecules for fluorimetric analysis of a variety of amines and for the elaboration of complex molecular architectures. Nevertheless, literature generally describes their synthesis in very low yield (below 5%), mainly due to the inefficiency of the last oxidation step. In this paper, we report a reliable synthesis of 4-substituted-ortho-phthalaldehyde analogues in 51% overall yield owing to the addition of a protecting step of the unstable key intermediate 4,5-dihydroisobenzofuran-5-ol. Oxidation and deprotection steps were also studied in order to provide an effective availability of these two dialdehyde compounds that may increase their future applications.
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Dates et versions

hal-02865852 , version 1 (22-07-2020)

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Clémence Moitessier, Ahmad Rifai, Pierre-Edouard Danjou, Isabelle Mallard, Francine Cazier-Dennin. Efficient synthesis of 4-substituted- ortho -phthalaldehyde analogues: toward the emergence of new building blocks. Beilstein Journal of Organic Chemistry, 2019, 15, pp.721-726. ⟨10.3762/bjoc.15.67⟩. ⟨hal-02865852⟩
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