Preparation of Phthalaldehydes by Hydrolysis of Aromatic <i>gem</i>-Tetrabromides

Zhu, Peter C.; Lu, Kaitao; Wang, Der-Haw

doi:10.1021/bk-2007-0967.ch007

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2019

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“…After completing the oxidation step with convincing results, the final step of the methoxy group removal was undertaken. Several studies showed that OPA reacts in the presence of water to form a cyclic 1,3-phthalandiol [21] or a dimer [22]. Taking this into account to access pure 4-HO-OPA, it was decided to go for anhydrous deprotection reaction, and in doing so, keeping the dialdehyde part untouched.…”

Section: Resultsmentioning

confidence: 99%

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

Moitessier¹,

Rifai²,

Danjou³

et al. 2019

Beilstein J. Org. Chem.

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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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Section: Resultsmentioning

confidence: 99%