Sulfuric Acid → 3-Hydroxy-2-naphthoic acid

HRID 2186545Notes

Reaction equation

HRID 2186545 reaction equation
[OH:1][C:2]1[C:11]([C:12]([O-:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[Na+].S(=O)(=O)(O)O>>[OH:1][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 236722972-Naphthalenecarboxylic acid, 3-hydroxy-, monosodium salt

Product 1

HCID 71043-Hydroxy-2-naphthoic acidYield 90%

Conditions

Temperature
160 °C

Procedure

To a 1 L autoclave, 800 g of aqueous solution containing 100 g of sodium 2-hydroxynaphthalene-3-carboxylate prepared by means of the Kolbe-Schmitt method was fed and heated to 160° C. An aqueous sulfuric acid solution (72%) was added dropwise to the solution over 50 minutes to adjust the pH of the mixture to 3.5. Then, the mixture was cooled to 80° C. at the rate of 0.4° C./min. At the same temperature, the mixture was filtrated to give 80.6 g of crystalline 2-hydroxynaphthalene-3-carboxylic acid.

Workup

  1. customprepared by means of the Kolbe-Schmitt method
  2. temperatureThen, the mixture was cooled to 80° C. at the rate of 0.4° C./min
  3. filtrationAt the same temperature, the mixture was filtrated

Sources & evidence

ORD record
ord-40d5e710604c424099929d9650a38174
Source dataset
uspto-grants-2002_06
Patent number
US06403827B1

Reaction notes

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