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

HRID 1881541Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1881541
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-72c77d7a66544600b52f427bdaadd3e7
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318796B2

Notizen zur Reaktion

Wird geladen…