Sodium Hydroxide → 9,10-Anthracenedione, 2,3-dihydro-1,4,5,8-tetrahydroxy-

HRID 1576869

Reaction equation

HRID 1576869 reaction equation
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9](N)[CH:10]=[C:11](S(O)(=O)=O)[C:12]=3[OH:17])[C:7](=[O:23])[C:6]=2[C:5](N)=[CH:4][C:3]=1S(O)(=O)=O.[OH-:29].[Na+].S(S([O-])=O)([O-])=[O:32].[Na+].[Na+]>>[CH2:3]1[C:2](=[O:1])[C:15]2[C:6](=[C:7]([OH:23])[C:8]3[C:13]([C:14]=2[OH:16])=[C:12]([OH:17])[CH:11]=[CH:10][C:9]=3[OH:32])[C:5](=[O:29])[CH2:4]1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 807444,5-Diamino-9,10-dihydro-1,8-dihydroxy-9,10-dioxoanthracene-2,6-disulphonic acid

Product 1

HCID 664859,10-Anthracenedione, 2,3-dihydro-1,4,5,8-tetrahydroxy-

Conditions

Temperature
70 °C

Procedure

The 1,8-dihydroxy-4,5-diaminoanthraquinone-2,7-disulfonic acid reaction mixture prepared as in Example 5c, was cooled to 70°C. It was then treated with 117 parts of 50% sodium hydroxide solution and 70 parts of sodium hydrosulfite. The mixture was heated to 78° to 100°C and held at that temperature for 1 hour. It was then cooled to 60°C and filtered. The product was washed with dilute sodium sulfate solution containing about 1% of sodium hydrosulfite and the washed cake was immediately slurried in 10 to 15% sulfuric acid. The filtration of the product and drying yielded 20 parts of leuco 1,4,5,8-tetrahydroxyanthraquinone.

Workup

  1. temperatureThe mixture was heated to 78° to 100°C
  2. temperatureIt was then cooled to 60°C
  3. filtrationfiltered
  4. washThe product was washed with dilute sodium sulfate solution
  5. additioncontaining about 1% of sodium hydrosulfite
  6. filtrationThe filtration of the product
  7. customdrying

Sources & evidence

ORD record
ord-134bc9b8315a4cd394c0caadfb0384ed
Source dataset
uspto-grants-1976_09
Patent number
US03983145

Linked notes

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