Abstract
Oxidation of 1,4-bis(4′-oxo-2′,2′-dimethylpent-2-yl)benzene with hypochlorite produces 1,4-bis(3′-carboxy-2′-methylbut-2-yl)benzene and 3-(4′-carboxyphenyl)-3,3-dimethylpropanoic acid. Cyclization of this mixture forms 3,3,7,7-tetramethyl-1,2,3,5,6,7-hexahydro-s-indacen-1,5-dione, 3,3,7,7-tetramethyl-1,2,3,5,6,7-hexahydro-as-indacen-1,5-dione (5) and 6-carboxy-3,3-dimethyl-1-indanone (6). Ketoacid (6) is converted to the arylpyran pseudoacid 7-carboxy-3-hydroxy-4,4-dimethylisobenzopyran-1-one (7). In the crystal structure of (7), carboxylic acid and the pseudoacid groups each form complementary dimer hydrogen bonds linking the molecules in chains. Contact O···O distances reflect their differing energetics, with pseudoacyl O···O at 2.78(1)Å and carboxylic O···O at 2.62(1)Å.
Graphical Abstract
A normal, pseudodiacid shows complementary hydrogen bonds between the two similar functions forming chains.
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Acknowledgments
The authors thank the National Science Foundation (MRI-0618148) for resources supporting diffraction equipment and the W. M. Keck Foundation for resources supporting spectroscopy.
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Milling, M.L., Cooley, J., Liskin, D.V. et al. Synthesis and structure of an arylpyran normal, pseudodiacid showing recognition. Struct Chem 20, 969–973 (2009). https://doi.org/10.1007/s11224-009-9499-8
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DOI: https://doi.org/10.1007/s11224-009-9499-8