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Volumn 65, Issue 9, 2000, Pages 2837-2842

Synthesis of 3,5-disubstituted 4-hydroxybenzoates by aryl-aryl and alkynyl-aryl coupling

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYBENZOIC ACID; ALKYNYL GROUP; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

EID: 0034607711     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991907m     Document Type: Article
Times cited : (24)

References (42)
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    • note
    • Benzofurans 9 and 13 have not been isolated from these experiments. They have been prepared separately from phenols 8 or 12 (Godt, A. Manuscript in preparation). With the help of the known NMR data of benzofurans 9 and 13, the side product of the deprotection step could be easily identified as the benzofuran. Characteristic signals are the doublets of the two protons in ortho position to the ester group above 8 ppm and the singlet at ca. 7.0 ppm caused by the proton at the furan ring. Representatively, the analytical data of 9c and 13c are given in the Supporting Information.
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    • 3,4-Dihydro-2H-pyran, TsOH monohydrate or pyridinium tosylate, diethyl ether, rt or 0 °C.
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    • 13C satellites of the singlet corresponding to the protons of the 4-hydroxybenzoate unit of compounds 7 or 8.
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    • note
    • Use of piperidine instead of triethylamine resulted in addition of piperidine onto the triple bond of the coupling product 4b.


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