Water → 2-Naphthol

HRID 1249640

Reaction equation

HRID 1249640 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1S([O-])(=O)=O.[Na+].[OH-:16].[Na+].O>C(C1C(CC2C=CC=CC=2)=C(C)C=CC=1)C1C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:16]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 23661868Sodium 2-naphthalenesulfonate

Product 1

HCID 86632-NaphtholYield 92.5%

Reagents, catalysts & solvents 1

HCID 3034397Methylbis(phenylmethyl)benzeneSolvent

Conditions

Temperature
300 °C

Procedure

Sodium naphthalene-2-sulfonate (230 g) was suspended in 795 g of dibenzyltoluene, and 176 g of a 50% aqueous solution of sodium hydroxide was added. The mixture was stirred under a nitrogen stream and heated to 300° C. to dehydrate it. The dehydrated mixture was stirred at 310° C. for 3 hours. After cooling, 1.2 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 133.2 g (yield 92.5%) of 2-naphthol.

Workup

  1. stirringThe dehydrated mixture was stirred at 310° C. for 3 hours
  2. temperatureAfter cooling
  3. customto separate the reaction medium layer
  4. customprecipitated with an acid

Sources & evidence

ORD record
ord-a364fb2dd81c4501b9d18df5c1bee329
Source dataset
uspto-grants-1986_12
Patent number
US04633024

Linked notes

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