Nitric Acid → 3-Nitro-4-propylbenzoic acid

HRID 365479

Reaktionsgleichung

Reaktionsgleichung von HRID 365479
[CH2:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)[CH2:2][CH3:3].[N+:13]([O-])([OH:15])=[O:14]>OS(O)(=O)=O>[N+:13]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:4]=1[CH2:1][CH2:2][CH3:3])[C:8]([OH:10])=[O:9])([O-:15])=[O:14]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 1376014-Propylbenzoic acid

Produkt 1

HCID 155216373-Nitro-4-propylbenzoic acidAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

9.44 g (57.5 mmol, 1.0 equiv.) of 4-propylbenzoic acid were partially dissolved in 50 mL conc. H2SO4 and chilled in an ice bath. A solution of 4.7 mL (74.7 mmol, 1.3 equiv) conc. HNO3 in 10 mL conc. H2SO4 was added dropwise over 1-2 min. After stirring 1 hour at 0° C., the reaction mixture was poured into a 1 L beaker half full with ice. After stirring 10 minutes, the white solid which formed was filtered, washed 1×H2O, and dried to give 12.01 g (100%) of the title compound: mp 106-109° C.; IR (KBr) 3200-3400, 2966, 2875, 2667, 2554, 1706, 1618, 1537, 1299, 921 cm-1 ; 1H NMR (300 MHz, DMSO-d6) d 0.90 (t, 3H, J=7.4 Hz), 1.59 (m, 2H), 2.82 (m, 2H), 7.63 (d, 1H, J=8.0 Hz), 8.12 (dd, 1H, J=1.7, 8.0 Hz), 8.33 (d, 1H, J=1.7 Hz); 13C NMR (75.5 MHz, DMSO-d6) d 14.2, 23.7, 34.2, 125.4, 130.5, 132.9, 133.6, 141.4, 149.5, 165.9; Anal. calcd for C10H11NO4.1/4H2O: C, 56.20; H, 5.42; N, 6.55. Found: C, 56.12; H, 5.31; N, 6.81.

Aufarbeitung

  1. temperaturechilled in an ice bath
  2. additionthe reaction mixture was poured into a 1 L beaker half full with ice
  3. stirringAfter stirring 10 minutes
  4. customthe white solid which formed
  5. filtrationwas filtered
  6. washwashed 1×H2O
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8f8a52a9e3e243b3a630542a063ea7ef
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127398

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