Methanol → 3-(4-Nitro-phenyl)-acrylic acid methyl ester
Reaction equation
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]=1Participants
4
Conditions
- Temperature
- 40 °C
Procedure
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 (71) (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).