Synthesis
General procedure for the synthesis of 2-amino-5-methylbenzenemethanol from 2-amino-5-methylbenzoic acid: lithium aluminum hydride (20.4 mmol) was suspended in tetrahydrofuran (THF, 10 mL) at room temperature, followed by slow dropwise addition of a solution of 2-amino-5-methylbenzoic acid (8.5 mmol) dissolved in THF (24 mL) over a period of 20 min. The reaction mixture was stirred continuously for 3.5 h at room temperature. Upon completion of the reaction, the reaction was carefully quenched with deionized water (10 mL) at 0 °C. The resulting suspension was filtered through a diatomaceous earth pad and the filter cake was washed well with ethyl acetate (EtOAc, 100 mL). The combined organic phases were washed with saturated saline (30 mL), dried over anhydrous magnesium sulfate (MgSO), and finally concentrated under reduced pressure to give the target product 2-amino-5-methylbenzyl alcohol.
References
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[2] Chemical Communications, 2017, vol. 53, # 1, p. 216 - 219
[3] Organic Letters, 2017, vol. 19, # 12, p. 3219 - 3222
[4] Tetrahedron Letters, 2017, vol. 58, # 40, p. 3795 - 3799
[5] Patent: US5190971, 1993, A
