Sulfuric Acid → 3-Hydroxy-1-naphthoic acid

HRID 434023

Reaktionsgleichung

Reaktionsgleichung von HRID 434023
[OH:1][C:2]1[CH:3]=[C:4]([C:27]([OH:29])=[O:28])[C:5]2[C:10]([C:11]=1N=NC1C(C)=NN(C3C=CC=CC=3)C=1O)=[CH:9][CH:8]=[CH:7][CH:6]=2.N([O-])=O.[Na+].S(=O)(=O)(O)O>O>[OH:1][C:2]1[CH:3]=[C:4]([C:27]([OH:29])=[O:28])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 178433866HCID 178433866, Verbindung

Produkt 1

HCID 1902323-Hydroxy-1-naphthoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of the compound from example 14 b) (8.73 g; 0.042 mol.) in water (300 mL) was treated with 2M aqu. sulfuric acid (60.0 mL) to precipitate the free acid as a fine powder. This suspension was then stirred and cooled to 10° then slowly treated dropwise with a solution of sodium nitrite (3.03 g; 0.044 mol.) in water (30.0 mL). After 30 min. at 10° the solution was added very slowly dropwise to a refluxing solution of 40% aqu. sulfuric acid (1 L). Complete addition took ˜1 h. After complete addition the mixture was heated under reflux for a further 15 min. then quickly hot-filtered through a plug of glass wool to remove insoluble, charred material. The filtrate was allowed to cool depositing the title compound (5.85 g; 74%) as yellow crystals. mp 210-212°. MS(ES) m/z 187 [M−H].

Aufarbeitung

  1. customsulfuric acid (60.0 mL) to precipitate the free acid as a fine powder
  2. temperaturecooled to 10°
  3. additionAfter 30 min. at 10° the solution was added very slowly dropwise to a refluxing solution of 40% aqu
  4. additionComplete addition
  5. additionAfter complete addition the mixture
  6. temperaturewas heated
  7. temperatureunder reflux for a further 15 min.
  8. filtrationthen quickly hot-filtered through a plug of glass wool
  9. customto remove insoluble
  10. temperatureto cool

Quellen und Nachweise

ORD-Eintrag
ord-994df1cb1f29476c928a5a53e856ba86
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06670387B1

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