Nitric Acid → 5-Nitronaphthalene-2,3-diol

HRID 400711

Reaktionsgleichung

Reaktionsgleichung von HRID 400711
[OH:1][C:2]1[C:11]([OH:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[N+:13]([O-])([OH:15])=[O:14]>C(OC(=O)C)(=O)C>[N+:13]([C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[C:11]([OH:12])[C:2]([OH:1])=[CH:3]2)([O-:15])=[O:14]

Komponenten

4

Edukt 2

HCID 944Nitric Acid2×HCID 70912,3-Dihydroxynaphthalene

Produkt 1

HCID 110527585-Nitronaphthalene-2,3-diol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

A suspension of 5.0 g of 2,3-Dihydroxynaphthalene dimesitylate in 50 ml of acetic anhydride was treated with 12 ml of 70% HNO3 at such a rate as to keep the temperature between 37-40° C. A cooling bath should be kept under the flask, ready to be raised if necessary, as the temperature should not be allowed to exceed 45° C. The 12.0 ml of nitric acid was added to the reaction mixture over a period of 1-2 h. After 2 h, the reaction mixture was cooled to 5° C. in an ice bath and the precipitate was collected by filtration and washed with ether. Yield 5-Nitro-2,3-dihydroxynaphthalene dimesitylate 70%; mp 199-201° C., 1H NMR (DMSO-d6) δ 3.58 (s, 6H), 7.76 (t, J=8.0 Hz, 1H), 8.25-8.65 (m, 4H)

Aufarbeitung

  1. custombetween 37-40° C
  2. customA cooling bath should be kept under the flask
  3. temperatureready to be raised if necessary, as the temperature should not
  4. customto exceed 45° C
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with ether

Quellen und Nachweise

ORD-Eintrag
ord-f07d4a1ca1ec419e81a8e1437d4c8e3f
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741917B2

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