Synthesis
Example 1: Preparation of ethyl 4-(aminomethyl)benzoate
Add 7.5 g (50 mmol) of 4-(aminomethyl)benzoic acid to a 250 mL three-necked round-bottomed flask. 100mL of anhydrous ethanol was added. Under the condition of ice bath, 20.8 g (175 mmol) of thionyl chloride was slowly added dropwise, and after completion of the dropwise addition, the reaction was stirred at room temperature for 30 min, followed by heating and refluxing for 4 hours. Upon completion of the reaction, the heating was stopped and the ethanol was removed by distillation under reduced pressure to give a white solid product. The resulting solid was dissolved in 150 mL of ethyl acetate, and the pH was adjusted to 7-8 by slowly adding 35% aqueous sodium hydroxide under the condition of an ice bath. the organic layer and the aqueous layer were separated, and the organic layer was washed with saturated saline three times, each time 30 mL. the organic layer was dried with anhydrous sodium sulfate, filtered, and concentrated to give a yellow solid product in 90% yield.
References
[1] Patent: CN104016942, 2016, B. Location in patent: Paragraph 0090; 0091; 0092
[2] Journal of the American Chemical Society, 1943, vol. 65, p. 2281,2283
[3] Organic and Biomolecular Chemistry, 2013, vol. 11, # 36, p. 6023 - 6028
[4] Journal of the American Society for Mass Spectrometry, 2018, vol. 29, # 4, p. 694 - 703
