Sodium Hydroxide → 5-Hydroxyisophthalic acid

HRID 1249643Notes

Reaction equation

HRID 1249643 reaction equation
S([C:5]1[CH:6]=[C:7]([C:14]([O-:16])=[O:15])[CH:8]=[C:9]([CH:13]=1)[C:10]([O-:12])=[O:11])(O)(=O)=O.[Na+].[Na+].[Na+].[OH-:20].[Na+].C1(C(C2C=CC=C(C)C=2C)C)C=CC=CC=1>O>[OH:20][C:5]1[CH:6]=[C:7]([C:14]([OH:16])=[O:15])[CH:8]=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 3033855Dimethyl(1-phenylethyl)benzeneHCID 20223815HCID 20223815, compound

Product 1

HCID 692575-Hydroxyisophthalic acidYield 94.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
280 °C

Procedure

Trisodium 5-sulfoisophthalate (312 g) was added to 170 g of a 50% aqueous solution of sodium hydroxide, and the mixture was stirred. Then, 1980 g of 1-phenyl-1-(2,3-dimethylphenyl)-ethane was mixed, and the resulting mixture was heated to 280° C. in a nitrogen stream and dehydrated with stirring. The dehydrated mixture was stirred at 280° C. for 1.5 hours. After cooling, 1 liter of water was added to the reaction mixture to separate the reaction medium. The aqueous layer was decolorized with activated carbon, and precipitated with dilute sulfuric acid to give 172.5 g (yield 94.8%) of 5-hydroxyisophthalic acid.

Workup

  1. stirringwith stirring
  2. stirringThe dehydrated mixture was stirred at 280° C. for 1.5 hours
  3. temperatureAfter cooling
  4. customto separate the reaction medium
  5. customprecipitated with dilute sulfuric acid

Sources & evidence

ORD record
ord-518834d0c8e6470688cdd7a9923409dc
Source dataset
uspto-grants-1986_12
Patent number
US04633024

Reaction notes

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