Carbon Dioxide → 6-Hydroxy-2-naphthoic acid

HRID 1734289Notes

Reaction equation

HRID 1734289 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].C(=O)=O.[CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[O-:20].[K+]>>[OH:20][C:11]1[CH:12]=[CH:13][C:14]2[C:19](=[CH:18][CH:17]=[C:16]([C:1]([OH:2])=[O:4])[CH:15]=2)[CH:10]=1

Participants

4

Reactant 3

HCID 280Carbon DioxideHCID 11430Potassium Carbonate2×HCID 236812372-Naphthalenol, potassium salt

Product 1

HCID 855576-Hydroxy-2-naphthoic acidYield 76%

Conditions

Temperature
280 °C

Procedure

A stainless steel pressure autoclave is charged with 50 parts of kerosene and 38 parts of potassium carbonate and heated to 280° C. It is then pressurized with 10 bar of carbon dioxide. Over the course of 5 hours, a mixture of 50 parts of potassium β-naphtholate and 38 parts of potassium carbonate are metered in as a suspension in kerosene via a metering pump, part of the kerosene being distilled off, condensed and transferred out of the reaction vessel at reduced pressure. After the usual workup, the 2-hydroxynaphthalene-6-carboxylic acid is obtained in a yield of 76% based on potassium naphtholate used. In addition, 14% of unreacted β-naphthol and small amounts of 2-hydroxynaphthalene-3-carboxylic acid and 2-hydroxynaphthalene-3,6-dicarboxylic acid are obtained.

Workup

  1. distillationdistilled off
  2. customcondensed

Sources & evidence

ORD record
ord-58eb986cc5b44461a84fcc0b3b5b1456
Source dataset
uspto-grants-1996_07
Patent number
US05532406

Reaction notes

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