Synthesis
The Phillips method [1] was used to synthesize (5-methyl-1H-benzimidazol-2-yl)methanol by heating at reflux for 3 h in hydrochloric acid (50 ml, 5.5 M) using 4-methyl-1,2-phenylenediamine (12.22 g; 0.1 mol) and ethanoic acid (11.40 g; 0.15 mol) as raw materials. After completion of the reaction, the mixture was cooled to room temperature, pH was adjusted by addition of aqueous ammonia solution and subsequently cooled in an ice bath until a bright brown precipitate was precipitated. Purification by recrystallization from aqueous ethanol gave (5-methyl-1H-benzimidazol-2-yl)methanol as a light creamy white powdery solid in 100% yield.
References
[1] Molecules, 2015, vol. 20, # 8, p. 15206 - 15223
[2] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 4, p. 1272 - 1274
[3] Russian Journal of General Chemistry, 2017, vol. 87, # 12, p. 3006 - 3016
[4] Patent: US2018/44324, 2018, A1. Location in patent: Paragraph 0614
[5] Chemische Berichte, 1912, vol. 45, p. 3495
