Neue, ungewöhnlich verlaufende Arylierungen der 1,5-Dihydroxy-4,8-diaminoanthrachinon-2,6-disulfonsäure mit Kresolen
✍ Scribed by Jean-Marie Adam; Peter Hindermann; Tammo Winkler
- Publisher
- John Wiley and Sons
- Year
- 1976
- Tongue
- German
- Weight
- 827 KB
- Volume
- 59
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
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 ^1^H‐ and ^13^C‐NMR. spectroscopy and the pattern of arylation reaction with phenol is discussed.