Hydrochloric Acid → Benzoic acid, 4-amino-3,5-dimethyl-, methyl ester

HRID 239922

Reaktionsgleichung

Reaktionsgleichung von HRID 239922
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:15])[C:11]=1[N+:12]([O-])=O)[C:5]([O:7][CH3:8])=[O:6].Cl>CO.[Fe]>[NH2:12][C:11]1[C:2]([CH3:1])=[CH:3][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][C:10]=1[CH3:15]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 22998442Methyl 3,5-dimethyl-4-nitrobenzoate

Produkt 1

HCID 11030398Benzoic acid, 4-amino-3,5-dimethyl-, methyl esterAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of methyl 3,5-dimethyl-4-nitrobenzoate (10.0 g, 0.0478 mol) in methanol (100 mL), iron powder (15.7 g, 0.2869 mol) and 37% HCl (1.72 g, 0.0478 mol) is added at 0° C. The reaction is heated at 80° C. for 16 hours. The mixture is cooled to room temperature and filtered through Celite™ bed and washed with methanol followed by evaporation of filtrate to dryness to afford the title compound as a brown solid (7.8 g, 99%). Mass spectrum (m/z): 180.2 (M+1).

Aufarbeitung

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationfiltered through Celite™ bed
  3. washwashed with methanol
  4. customfollowed by evaporation of filtrate to dryness

Quellen und Nachweise

ORD-Eintrag
ord-bdf5542c7db34ce893fb48daf8b10c3c
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642768B2

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