2-(4-Phenoxybenzoyl)benzoic acid → 2-Hydroxyanthraquinone

HRID 1680796

Reaction equation

HRID 1680796 reaction equation
[O:1]([C:8]1[CH:21]=[CH:20][C:19]2[C:18](=[O:22])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:23])[C:10]=2[CH:9]=1)C1C=CC=CC=1.O(C1C=CC(C(C2C=CC=CC=2C(O)=O)=O)=CC=1)C1C=CC=CC=1.O(C1(S([O-])(=O)=O)C=CC2C(=O)C3C(=CC=CC=3)C(=O)C=2C1S([O-])(=O)=O)C1C=CC=CC=1.[Na+].[Na+]>>[OH:1][C:8]1[CH:21]=[CH:20][C:19]2[C:18](=[O:22])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:23])[C:10]=2[CH:9]=1

Participants

4

Reactant 3

HCID 7465192-(4-Phenoxybenzoyl)benzoic acidHCID 124905002-Phenoxyanthracene-9,10-dione2×HCID 20530050HCID 20530050, compound

Product 1

HCID 117962-Hydroxyanthraquinone

Procedure

2-phenoxyanthraquinonedisulfonic acid formed as an intermediate product in the course of preparing 2-phenoxyanthraquinonepolysulfonic acid from 2-phenoxyanthraquinone or 2-(p-phenoxybenzoyl) benzoic acid was confirmed, by way of a proton-NMR-absorption spectrum thereof, as having such a structure that the two sulfonic acid groups are bonded, as shown in the reaction formulas (1), to o- and p-positions of the phenoxy group in the 2-phenoxyanthraquinone. FIG. 3 shows a proton-NMR-absorption spectrum (solvent: dimethylacetamide; measuring temp.: room temperature) of sodium 2-phenoxyanthraquinonedisulfonate. This spectrum shows that in the compound of the formula (VII): ##STR11## absorption of proton f is detected in 8.44 ppm (1H), absorption of protons c, h in 8.04-8.3 ppm (3H), absorption of protons e, g in 7.83-8.02 ppm (3H), absorption of proton a in 7.61 ppm (1H), absorption of proton b in 7.42 ppm (1H) and absorption of proton d in 7.1 ppm (1H). It is confirmed therefore that 2-phenoxyanthraquinonedisulfonic acid has the structure shown by the formula (VII). The structure of the formula (VII) is supported also by the fact that when this 2-phenoxyanthraquinonedisulfonic acid is treated under heating with a 5% aqueous solution of sodium hydroxide, the phenoxy group of this compound is split off to afford 2-hydroxyanthraquinone.

Workup

  1. custom##STR11## absorption of proton f
  2. customis detected in 8.44 ppm (1H), absorption of protons c, h in 8.04-8.3 ppm (3H), absorption of protons e
  3. customg in 7.83-8.02 ppm (3H), absorption of proton a
  4. customin 7.61 ppm (1H), absorption of proton b
  5. customin 7.42 ppm (1H) and absorption of proton
  6. additionis treated
  7. temperatureunder heating with a 5% aqueous solution of sodium hydroxide
  8. customthe phenoxy group of this compound is split off

Sources & evidence

ORD record
ord-da0b7d225b3b46e0bc4af53c0d40354d
Source dataset
uspto-grants-1981_06
Patent number
US04276187

Linked notes

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