Sulfuric Acid → 3-Hydroxy-4-(methoxycarbonyl)benzoic acid

HRID 2103808Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2103808
N[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:5]([OH:7])=[O:6].N([O-])=[O:16].[Na+].S(=O)(=O)(O)O>Cl.C(O)(=O)C>[OH:16][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:5]([OH:7])=[O:6]

Komponenten

6

Edukt 3

HCID 1118Sulfuric AcidHCID 52355003-Amino-4-(methoxycarbonyl)benzoic acidHCID 23668193Sodium Nitrite

Produkt 1

HCID 670501783-Hydroxy-4-(methoxycarbonyl)benzoic acidAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

To 3-amino-4-methoxycarbonylbenzoic acid (1.95 g, 10 mmol) suspended in 3 M hydrochloric acid (12.5 mL) and acetic acid (20 mL), an aqueous solution (20 mL) of sodium nitrite (0.69 g, 10 mmol) was added at −10° C., and the resulting solution was stirred for 30 minutes. The solution was added to 10% aqueous sulfuric acid (30 mL) at 0° C., and the resulting reaction mixture was heated with reflux for 1 hour. The desired product was extracted with ethyl acetate, and the extract was dried over magnesium sulfate and purified by silica gel column chromatography to give 1.04 g of the desired product as a white solid (yield 53%).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. temperaturewas heated
  3. temperaturewith reflux for 1 hour
  4. extractionThe desired product was extracted with ethyl acetate
  5. dry with materialthe extract was dried over magnesium sulfate
  6. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1abfb2ad3ace4d42a22d9ecef366eb3c
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576115B2

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