Synthesis
A reduction reaction was carried out using 4-hydroxymethylbenzonitrile (2.0 g, 15 mmol) as a raw material in MeOH:NH3 (100 ml) solution under hydrogen (50 psi) atmosphere for 20 hrs using nickel Nguyenay (0.5 g) as a catalyst. Upon completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad to remove the catalyst. The filtrate was concentrated under reduced pressure to afford a white solid (4-aminomethylphenyl) methanol hydrochloride (2.01 g, 98% yield), which was pure enough to be used directly in the subsequent reaction without further purification. The product characterization data were as follows: mass spectrum (APCI+): m/z 138.3 (M+H)+; 1H-NMR (DMSO-d6) δ 7.20 (s, 4H), 5.04 (s, 2H), 4.42 (s, 2H), 3.83 (s, 1H), 2.45 (s, 2H).
References
[1] Patent: WO2005/56004, 2005, A1. Location in patent: Page/Page column 154-155
[2] ACS Catalysis, 2018, vol. 8, # 10, p. 9125 - 9130
[3] Journal of Organic Chemistry, 1998, vol. 63, # 22, p. 7663 - 7669
[4] Patent: US2015/259291, 2015, A1. Location in patent: Paragraph 0612
[5] Patent: WO2007/124136, 2007, A1. Location in patent: Page/Page column 130
