Synthesis
General procedure for the synthesis of m-(methoxymethyl)aniline from 1-(methoxymethyl)-3-nitrobenzene: 3-(methoxymethyl)nitrobenzene (4.18 g, 25 mmol) from the previous step was dissolved in 160 mL of acetic acid. Zinc powder (5 g, 76.5 mmol) was added to the solution and the reaction mixture was stirred at room temperature for 18 h until HPLC analysis showed no 3-(methoxymethyl)nitrobenzene residue. Upon completion of the reaction, the mixture was filtered through diatomaceous earth and the filtrate was subsequently concentrated under vacuum. The concentrated residue was dissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate. The organic layer was further washed with water and dried with anhydrous magnesium sulfate. Finally, the dried organic phase was concentrated under vacuum to give 3.4 g (99% yield) of the target product 3-(methoxymethyl)aniline as a brown oil.
References
[1] European Journal of Organic Chemistry, 2015, vol. 2015, # 10, p. 2282 - 2290
[2] Journal of the American Chemical Society, 2010, vol. 132, # 50, p. 17910 - 17920
[3] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 3, p. 1430 - 1438
[4] Journal of the Chemical Society, 1954, p. 4127,4132
[5] Zhurnal Obshchei Khimii, 1955, vol. 25, p. 2290,2292; engl. Ausg. S. 2259, 2261
