Beilstein J. Org. Chem.2019,15, 721–726, doi:10.3762/bjoc.15.67
– National Council for Scientific Research – B. P. 11- 8281, Riad El Solh 1107, 2260 Beirut, Lebanon 10.3762/bjoc.15.67 Abstract 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
; hydroxy group protection; 4-hydroxy-ortho-phthalaldehyde; ortho-phthalaldehyde; oxidation; Introduction
Benzene-1,2-dicarboxaldehyde, also called ortho-phthalaldehyde (OPA) was employed in different domains such as in analytical and organic chemistry. In fact, it is one of the most commonly used
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Graphical Abstract
Scheme 1:
Synthesis of 4,5-dihydroisobenzofuran-5-ol (3).
Beilstein J. Org. Chem.2018,14, 182–186, doi:10.3762/bjoc.14.12
and hexafluoroacetone to give 3-(trifluoromethyl)phthalide derivatives [11]. In 2006, Pedrosa et al. reported the nucleophilic trifluoromethylation of protected ortho-phthalaldehyde, followed by deprotection and oxidation to afford 3-(trifluoromethyl)phthalide [12]. Pohmakotr et al. demonstrated the
asymmetric synthesis of 3-(trifluoromethyl)phthalide (1a) using a chiral auxiliary was published to date. In 2006, Pedrosa and co-workers discribed the diastereoselective nucleophilic trifluoromethylation of aldehyde 5, which was prepared by condensation of ortho-phthalaldehyde with (−)-8-benzylaminomenthol
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Graphical Abstract
Scheme 1:
Phthalide and fluorinated phthalides (1).