2-Ethoxybenzonitrile

To a 250 mL three-necked flask, 5.95 g (0.05 mol) of o-cyanophenol, 20 mL of 10percent aqueous NaOH solution and 80 mL of toluene were separately added, and the mixture was heated to 70 ° C, and the reaction was kept at this temperature for 1 h. After 1 h, the temperature was lowered to 60 ° C, and 9.24 g of diethyl sulfate was slowly added dropwise.After the dropwise addition, the temperature was raised to 70 ° C and the reaction was continued for 2 h. The disappearance of o-cyanophenol was detected by TLC, and the mixture was cooled to separate liquid. The toluene layer was evaporated to give a pale yellow oily liquid, 2-ethoxybenzonitrile, 6.98 g, yield 95percent.11.9 g (0.1 mol) of salicylic acid nitrile, 100 mL of toluene, and 48 g of 10percent aqueous NaOH solution were sequentially added to a 250 mL four-necked flask under stirring.The temperature was raised to 68 ° C in a water bath, and the mixture was kept for 1 hour, and then 9.2 g (0.06 mol) of diethyl sulfate was added dropwise, and after the completion of the dropwise addition, the temperature was raised to 75 ° C, and the reaction was kept for 1 hour.The temperature was lowered to 68 ° C, and 9.2 g (0.06 mol) of diethyl sulfate was added dropwise. After the completion of the dropwise addition, the temperature was raised to 75 ° C, and the reaction was kept for 2 hours. The TLC tracking was carried out until the salicylonitrile was completely reflected.Cooling, liquid separation, collecting the organic layer, drying with anhydrous sodium sulfate, and then evaporating the toluene solvent, A yellowish oily liquid was obtained in an amount of 13.7 g, a yield of 93percent, and a gas-mass spectrometric analysis content of 97percent.4.2 General procedure: BrCClUnder nitrogen protection, 200 mL of ethanol, cuprous iodide (3.8 g, 0.02 mol) and potassium hydroxide (16.8 g, 0.3 mol) were mixed uniformly, O-chlorobenzonitrile (27.5 g, 0.2 mol) was added, And then heated to 80 insulation reaction, TLC or liquid phase monitoring reaction, After completion of the reaction, ethanol was recovered, Down to room temperature, Add 100 mL of water and 150 ml of toluene to wash with water, And then toluene recovery, The intermediate of o-ethoxybenzene was purified by distillation under reduced pressure (23.5 g (154 ° C / 20 Torr). 20.6 g (0.14 mol) of o-ethoxybenzonitrile was dissolved in 150 mL of toluene, potassium tert-butoxide (47.1 g, 0.42 mol), heated to 60 ° C to carry out the reaction, TLC or liquid phase monitoring reaction, the reaction is completed by adding 150mL of water for washing, The organic phase recovered the solvent and the residue was recrystallized from ethanol and dried to give 19.7 g of 2-ethoxybenzamide as a white solid.

Molecular Weight:147.17
XLogP3:2.3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:147.068413911
Monoisotopic Mass:147.068413911
Topological Polar Surface Area:33
Heavy Atom Count:11
Complexity:158
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes