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ChemicalBook CAS DataBase List 2-Methoxybenzonitrile

2-Methoxybenzonitrile synthesis

11synthesis methods
o-Anisidine with sodium nitrite to make a diazonium salt solution, add it to the lead cyanide solution, and then add benzene. Put the mixture for 10-15h and carry out steam distillation, separate the benzene layer from the distillate, dry it with calcium chloride, evaporate the benzene, and distill the residue under reduced pressure, collect 120-122.5°C (1.2kPa fraction) to get 2-Methoxybenzonitrile, yield 64.5-67.3%.
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Yield:6609-56-9 98%

Reaction Conditions:

with trifluorormethanesulfonic acid;trimethylsilylazide in acetonitrile at 25; for 0.00138889 h;Flow reactor;Schmidt Reaction;

Steps:



General procedure: General procedure for synthesis of nitriles from aldehydes incontinuous ow is as follows. Take benzaldehyde as an example,benzaldehyde (0.6 mmol) and TfOH (0.9 mmol) were dissolved in3 mL MeCN and pumped into inlet A. TMSN 3 (0.6 mmol) wasdissolved in 3 mL MeCN and pumped into inlet B (ow rate A:B = 54 m L/min:65 m L/min for 5 s residence time). The whole systemwas maintained at 25C. The ow system was equilibrated (about5 min), then the product stream was quenched and collected in aglass vessel with saturated aqueous NaClO in it. The ow systemwas stopped after the inlet A reduced 0.5 mL. The crude mixturewas dissolved in ethyl acetate and washed with saline solution. Thecombined organic layers were dried over magnesium sulfate,ltered, and concentrated under reduced pressure. The resultingcrude product was puried by ash chromatography on silica gelwith hexane and EtOAc as eluent to afford the product

References:

Zhan, Wei;Tong, Meng;Ji, Ling;Zhang, Han;Ge, Zemei;Wang, Xin;Li, Runtao [Chinese Chemical Letters,2019,vol. 30,# 5,p. 973 - 976]

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