Dimethylformamide → ethyl 3-methyl-4-nitrobenzoate

HRID 962942Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 962942
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].CN(C)C=O.C(=O)(O)[O-].[Na+].I[CH2:25][CH3:26]>O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([O:7][CH2:25][CH3:26])=[O:6]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 183703-Methyl-4-nitrobenzoic acidHCID 516892Sodium Bicarbonate

Produkt 1

HCID 2796918ethyl 3-methyl-4-nitrobenzoateAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 3-methyl-4-nitrobenzoic acid (1) (362.3 g, 2.0 mol), N,N-dimethylformamide (2000 mL), sodium bicarbonate (200 g, 2.38 mol) and iodoethane (623.9 g, 4.0 mol) was stirred at 70° C. for 18 h. The mixture was allowed to cool to room temperature and poured into water (2000 mL. The resulting solid was collected by filtration, washed with water and dried. The solid was washed further with hexane and dried to provide the title product (382.1 g, 91%) as an off-white solid: mp 51°-52.5° C.; 1H NMR (CDCl3) δ 8.04-7.98 (m, 3H), 4.42 (q, 2H), 2.63 (s, 3H), 1.42 (t, 3H); Mass spectrum (NH3 --CI) m/z 210 (100%, M+H+).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water
  4. customdried
  5. washThe solid was washed further with hexane
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-767328e277a949d89df8211e8f23f8dd
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05760028

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