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    Author(s): Gerald W. McGraw; Peter E. Laks; Richard W. Hemingway
    Date: 1988
    Source: Journal Wood Chemistry & Technology 8(1):91-109
    Publication Series: Miscellaneous Publication
    PDF: View PDF  (2.2 MB)


    Studies on the desulfonation of 2,4,6-trihydroxybenzylsufonic acid and sodium epicatechin-(4β)-sulfonate showed that suflonates to α a phloroglucinol ring are good leaving groups at ambient temperature and pH greater than 8.0. In contrast, hydroxybenzylsufonic acids with resorcinol or phenol hydroxl functionality resist desulfonation even at pH 12 and 90°C. It was also not possible to make (2,4,6-trihydroxyphenyl), (4-hydroxyphenyl)-methane or (2,4,6-trihydroxyphenyl), (2,4-dihydroxyphenyl)-methane by slow addition of 2,4,6-trihydroxybenzyl-sulfonic acid to alkaline solutions of phenol or resorcinol.

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    McGraw, Gerald W.; Laks, Peter E.; Hemingway, Richard W. 1988. Condensed tannins: Desulfonation of hydrox-benzylsufonic acids related to proanthocyanidin derivatives. Journal Wood Chemistry & Technology 8(1):91-109

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