Benzenebutanenitrile, 3,5-dimethoxy- synthesis
- Product Name:Benzenebutanenitrile, 3,5-dimethoxy-
- CAS Number:1057672-62-4
- Molecular formula:C12H15NO2
- Molecular Weight:205.25
Yield:1057672-62-4 85%
Reaction Conditions:
in N,N-dimethyl-formamide at 50; for 24 h;
Steps:
NaCN (1.08 g, 22.02 mmol) was added to a solution of alkyl bromide 10 (1.90 g, 7.34 mmol) in DMF (25 ml) at 50 C. The reaction mixture was stirred at the same temperature for 24 h. After the mixture was cooled to room temperature, EtOAc (80 ml) and H2O (20 ml) were added to this mixture. The organic layer was separated and extracted with H2O (320 ml). The organic phase was dried over Na2SO4 and the solvent was evaporated. Chromatography of the residue on asilica-gel column (30 g) with 30% EtOAc-hexane gave colorless liquid nitrile 11 (1.28 g, 85%). 1H NMR (400MHz, CDCl3) d 6.33 (s, 3H, Ar-H), 3.77 (s, 6H, 2OCH3), 2.71 (t, 2H, CH2, J7.4 Hz), 2.31 (t, 2H, CH2, J7.4 Hz), 1.96 (quintet, 2H, CH2, J7.4 Hz). 13C NMR (100MHz, CDCl3) d 161.22 (2C), 142.30 (C), 119.80 (CN), 106.41 (2CH), 98.50 (CH), 55.52 (2OCH3), 34.84 (CH2), 26.94 (CH2), 16.59 (CH2). IR (CH2Cl2, cm1): 3001, 2939, 2840, 2246, 1732, 1597, 1463, 1430, 1349, 1325, 1294, 1255, 1205, 1154, 1071, 940. Anal. calcd. for C12H15NO2: C, 70.22; H, 7.37; N, 6.82. Found: C, 70.18; H, 7.39; N, 6.80.
References:
Yilmaz, Süleyman;G?ksu, Süleyman [Synthetic Communications,2014,vol. 44,# 8,p. 1058 - 1065] Location in patent:supporting information
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