Water → 2,6-Dihydroxynaphthalene

HRID 1249642Notes

Reaction equation

HRID 1249642 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7](S([O-])(=O)=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1S([O-])(=O)=O.[K+].[K+].[OH-:21].[K+].[OH2:23]>>[OH:21][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[C:7]([OH:23])[CH:6]=2)[CH:1]=1

Participants

4

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 22725783HCID 22725783, compound

Product 1

HCID 935522,6-DihydroxynaphthaleneYield 92.6%

Conditions

Temperature
310 °C

Procedure

Dipotassium 2,6-naphthalenedisulfonate (364 g) was added to 560 g of a 50% aqueous solution of potassium hydroxide, and the mixture was stirred. Then, 2500 g of a hydrogenated triphenyl mixture was mixed, and the resulting mixture was heated to 310° C. in a nitrogen stream and dehydrated with stirring. The mixture was then stirred at 310° C. for 3 hours. After cooling, 2 liters of water was added to the reaction mixture to separate the hydrogenated triphenyl layer. The aqueous layer was decolorized with activated carbon, and precipitated with dilute sulfuric acid to give 148.2 g (yield 92.6%) of 2,6-dihydroxynaphthalene.

Workup

  1. stirringwith stirring
  2. stirringThe mixture was then stirred at 310° C. for 3 hours
  3. temperatureAfter cooling
  4. customto separate the hydrogenated triphenyl layer
  5. customprecipitated with dilute sulfuric acid

Sources & evidence

ORD record
ord-99b13d48e599415488937374abb58f76
Source dataset
uspto-grants-1986_12
Patent number
US04633024

Reaction notes

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