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- Title
Neue, ungewöhnlich verlaufende Arylierungen der 1,5-Dihydroxy-4,8-diaminoanthrachinon-2,6-disulfonsäure mit Kresolen.
- Authors
Adam, Jean-Marie; Hindermann, Peter; Winkler, Tammo
- Abstract
A novel course of a phenylation reaction of 1,5-dihydroxy-4,8-diaminoanthraquin-one-2,6-disulfonic acid with cresols. The arylation of 1,5-dihydroxy-4,8-diaminoanthraquinone-2,6-disulfonic acid with m-cresol in conc. sulfuric acid gives in the presence of boric acid a mixture of monosulfonic acids which differ in the substitution of the m-cresol moiety. The main product ( 8, 95%) is substituted at the p-position to the methyl group, the side product ( 12, 5%) at the p-position to the OH group. The monosulfonic acid 8, which could not be isolated is further sulfonated under the reaction conditions to the disulfonic acid 9. In the case of o-cresol, the cresol moiety is substituted in the p-position ( 16) to OH group and in the case of p-cresol in the o-position ( 20) to OH group. The obtained monosulfonic acids 16 and 20 resp. are partially sulfonated further under the reaction conditions. The new structures are elucidated by 1H- and 13C-NMR. spectroscopy and the pattern of arylation reaction with phenol is discussed.
- Publication
Helvetica Chimica Acta, 1976, Vol 59, Issue 8, p2999
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19760590838