Carbon Dioxide → 3-Hydroxy-2-naphthoic acid

HRID 1734290Notes

Reaction equation

HRID 1734290 reaction equation
[C:1](=[O:4])([O-])[O-:2].[Na+].[Na+].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].[Na+]>>[OH:20][C:11]1[C:12]([C:1]([OH:2])=[O:4])=[CH:13][C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=1

Participants

4

Reactant 3

HCID 280Carbon DioxideHCID 10340Sodium CarbonateHCID 23664630Sodium 2-naphtholate

Product 1

HCID 71043-Hydroxy-2-naphthoic acidYield 65%

Conditions

Temperature
240 °C

Procedure

A stainless steel pressure autoclave is charged with 150 parts of kerosene and 32 parts of sodium carbonate and heated to 240° C. It is then pressurized with 10 bar of carbon dioxide. Over the course of 6 hours, 50 parts of sodium β-naphtholate 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-3-carboxylic acid is obtained in a yield of 65% based on sodium β-naphtholate used. In addition, 23% of unreacted β-naphthol and small amounts of 2-hydroxynaphthalene-6-carboxylic acid and 2-hydroxynaphthalene-3,6-dicarboxylic acid are obtained.

Workup

  1. distillationdistilled off
  2. customcondensed

Sources & evidence

ORD record
ord-0460b766a419471d8f69035e86576f97
Source dataset
uspto-grants-1996_07
Patent number
US05532406

Reaction notes

Loading…