Synthesis
General procedure for the synthesis of (2-amino-4-methylphenyl)methanol from (4-methyl-2-nitrophenyl)methanol: General method: (4-methyl-2-nitrophenyl)methanol (12) was dissolved in ethanol (concentration 0.2 M) and palladium/carbon catalyst (10% w/w, 5 mol%) was added. The reaction mixture was stirred for 1 h at room temperature under hydrogen atmosphere. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad and washed several times with ethyl acetate. The filtrate was concentrated under reduced pressure to obtain the crude product aniline, which was subsequently precipitated in a solvent mixture of petroleum ether and ethyl acetate (9:1, v/v). The precipitate was filtered and the solid was washed three times with a solvent mixture of the same ratio to give the final target product (2-amino-4-methylphenyl)methanol (11).
References
[1] Synlett, 2017, vol. 28, # 14, p. 1724 - 1728
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831
