Disodium 3-hydroxynaphthalene-2,7-disulfonate → 2-Naphthalenesulfonic acid, 6,7-dihydroxy-

HRID 1249645Notes

Reaction equation

HRID 1249645 reaction equation
[OH:1][C:2]1[C:11](S([O-])(=O)=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:16]([O-:19])(=[O:18])=[O:17])[CH:8]=2)[CH:3]=1.[Na+].[Na+].[OH-:22].[Na+]>O>[OH:1][C:2]1[C:11]([OH:22])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:16]([OH:19])(=[O:18])=[O:17])[CH:8]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 8673Disodium 3-hydroxynaphthalene-2,7-disulfonateHCID 14798Sodium Hydroxide

Product 1

HCID 667022-Naphthalenesulfonic acid, 6,7-dihydroxy-Yield 96.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Disodium 2-hydroxynaphthalene-3,6-disulfonate (348 g) was added to 176 g of a 50% aqueous solution of sodium hydroxide, and the mixture was stirred. Then, 900 g of a hydrogenated triphenyl mixture was mixed, and the resulting mixture was dehydrated. The dehydrated mixture was reacted at 270° C. for 1.5 hours in a nitrogen stream. After cooling, 2 liters of water was added to the reaction mixture to separate the reaction medium layer. The aqueous layer was decolorized with activated carbon, and then precipitated with an acid to give 231 g (yield 96.3%) of 2,3-dihydroxynaphthalene-6-sulfonic acid.

Workup

  1. customThe dehydrated mixture was reacted at 270° C. for 1.5 hours in a nitrogen stream
  2. temperatureAfter cooling
  3. customto separate the reaction medium layer
  4. customprecipitated with an acid

Sources & evidence

ORD record
ord-54f59e3a42924de8997dced75f9460e0
Source dataset
uspto-grants-1986_12
Patent number
US04633024

Reaction notes

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