3-Methoxy-4-methylbenzonitrile

Class white powder

C.14.d. 3-Methoxy-4-methylbenzonitrile 15 g (0.11 mol) of 3-hydroxy-4-methylbenzonitrile dissolved in 30 ml of DMF were added dropwise to a suspension of 0.11 mol of NaH and 30 ml of DMF and stirred until no further evolution of H2 was observed. Then 10.6 ml (0.17 mol) of methyl iodide were added dropwise, and the mixture was stirred at RT for 1 h. The solution was poured into ice-water, and the product was extracted with 7:1 ether/ethyl acetate. After the solvent was stripped off, the product began slowly to crystallize. 14.8 g (89%) of the product were obtained. 1H-NMR (CDCl3; delta in ppm): 7.2 (m, 2H); 7.02 (s, 1H); 3.85 (s, 3H); 2.25 (s, 3H)(d) 3-Methoxy-4-methylbenzonitrile 15 g (0.11 mol) of 3-hydroxy-4-methylbenzonitrile dissolved in 30 ml of DMF were added dropwise to a suspension of 0.11 mol of NaH in 30 ml of DMF, and the mixture was stirred until no further H2 evolution was observed. Then 10.6 ml (0.17 mol) of methyl iodide were added dropwise, and the mixture was stirred at room temperature for 1 h. The solution was poured into ice-water, and the product was extracted with ether/ethyl acetate 7:1. After the solvent had been stripped off, the product began to crystallize slowly. 14.8 g (89%) were obtained. 1 H-NMR (CDCl3; delta in ppm): 7.2 (m, 2H); 7.02 (s, 1H); 3.85 (s, 3H); 2.25 (s, 3H).To the reaction mixture was added while stirring and cooling with ice 120 milliliters of pyridine in small portions and further 550 milliliters of water. Crystals precipitated were separated by filtration, suspended in 200 milliliters of a 5% aqueous sodium hydroxide solution, and then stirred at room temperature for 30 minutes. These crystals were separated by filtration and the crude product thus obtained was purified by steam distillation to obtain 36.5 grams of 3-methoxy-4-methylcyano-benzene (yield, 84%).Under an inert atmosphere, to a solution of In a four-pot reaction flask, 100 g of 4-methyl-3-methoxybenzamide (I) (0.605 mol), 400 g of toluene, and 108 g of thionyl chloride (0.908 mol) were added, and the reaction was heated to 110C under reflux. After 4 hours, the spotting board traces the disappearance of raw materials, cools down, decompresses the solvent and excess thionyl chloride, and obtains the crude product. The crude product is beaten with 200 g of petroleum ether for 2 hours, filtered, and the filter cake is washed with petroleum ether, dried and baked. Dry yields 85 g of To a solution of

Molecular Weight:147.17
XLogP3:2.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:147.068413911
Monoisotopic Mass:147.068413911
Topological Polar Surface Area:33
Heavy Atom Count:11
Complexity:170
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes