Synthesis
GENERAL PROCEDURE: A solution was prepared by dissolving 2-amino-3-methylbenzoic acid (8.5 mmol) in THF (24 mL) at room temperature. In a separate vessel, a suspension of lithium aluminum hydride (20.4 mmol) in THF (10 mL) was prepared. The benzoic acid solution was added dropwise to the lithium aluminum hydride suspension over a period of 20 minutes. After the dropwise addition, the reaction mixture continued to be stirred at room temperature for 3.5 hours. Upon completion of the reaction, the reaction mixture was cooled to 0 °C and quenched by slow addition of H2O (10 mL). Subsequently, the suspension was filtered through a diatomaceous earth plug and washed with EtOAc (100 mL). The organic phase was washed with brine (30 mL), dried over anhydrous MgSO4 and finally concentrated under vacuum to give 2-amino-3-methylbenzyl alcohol.
References
[1] Chemical Communications, 2017, vol. 53, # 1, p. 216 - 219
[2] Organic Letters, 2017, vol. 19, # 12, p. 3219 - 3222
[3] Tetrahedron Letters, 2017, vol. 58, # 40, p. 3795 - 3799
[4] Journal of the American Chemical Society, 2014, vol. 136, # 24, p. 8729 - 8737
[5] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 655 - 662
