Methanol → 3-(4-Nitro-phenyl)-acrylic acid methyl ester

HRID 1362560

Reaktionsgleichung

Reaktionsgleichung von HRID 1362560
S(Cl)(Cl)=O.[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[CH:15][C:16]([OH:18])=[O:17])=[CH:10][CH:9]=1)([O-:7])=[O:6].[CH3:19]O>>[CH3:19][O:17][C:16](=[O:18])[CH:15]=[CH:14][C:11]1[CH:10]=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:13][CH:12]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 701562-Propenoic acid, 3-(4-nitrophenyl)-

Produkt 1

HCID 2196853-(4-Nitro-phenyl)-acrylic acid methyl ester

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Thionyl chloride (28.8 ml, 0.4 mol) was added dropwise to methanol (450 ml) at −10° C. temperature. To the obtained solution was added 3-(4-nitrophenyl)-acrylic acid (1) (38.63 g, 0.2 mol) and the reaction mixture was stirred at 0° C. for 3 hours, at ambient temperature for 24 hours and at 40° C. for 1 hour. The resulting precipitate was filtered, washed with methanol (2×10 ml) and dried affording the title compound in a form of yellow crystals (39.55 g, 96%). 1H NMR (DMSO-d6, HMDSO), δ: 3.69 (2H, br s); 3.77 (3H, s); 6.87 (1H, d, J=16.0 Hz); 7.67-8.39 (5H, m).

Aufarbeitung

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with methanol (2×10 ml)
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-212038e1d6894f37ae9eae937878cd6b
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07880020B2

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