Nitric Acid → 6-Nitro-1,3-benzodioxole-5-carboxylic acid

HRID 370088

Reaktionsgleichung

Reaktionsgleichung von HRID 370088
[C:1]([C:4]1[CH:12]=[CH:11][C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=1)([OH:3])=[O:2].[N+:13]([O-])([OH:15])=[O:14]>FC(F)(F)C(O)=O>[C:1]([C:4]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=1)([OH:3])=[O:2]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 71961,3-Benzodioxole-5-carboxylic acid

Produkt 1

HCID 2464356-Nitro-1,3-benzodioxole-5-carboxylic acidAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 5-carboxy-1,3-benzodioxole (50 g, 300 mmol) in trifluoroacetic acid (400 mL) at 0° C. was added HNO3 (38 mL, 900 mmol) dropwise. The reaction mixture was stirred at 0° C. for 1 hour, then warmed to ambient temperature and stirred for 3 hours. The mixture was poured into ice water and the resulting precipitate was collected by filtration. The solid was air dried overnight to afford 58 g (92% yield) of 5-carboxy-6-nitro-1,3-benzodioxole as a yellow solid; NMR (DMSO-d6) 7.6 (s, 1), 7.3 (s, 1), 6.3 (s, 2) ppm.

Aufarbeitung

  1. temperaturewarmed to ambient temperature
  2. stirringstirred for 3 hours
  3. filtrationthe resulting precipitate was collected by filtration
  4. customdried overnight

Quellen und Nachweise

ORD-Eintrag
ord-a0ba043c681b42faa33e8063dba41e31
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06140351

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