6702-50-7

Off-white to beige crystalline powder

To a dry 100 mL three-necked flask, 10 g of 3-hydroxy-4-methoxybenzoic acid, 110 mL of methanol, and 360 μL of concentrated sulfuric acid were sequentially added, and the mixture was heated to 65 °C and reacted under magnetic stirring overnight. The reaction process was monitored by thin layer chromatography (unfolding agent: ethyl acetate/dichloromethane=1:1). Upon completion of the reaction, the reaction mixture was transferred to a round bottom flask and methanol was removed by distillation under reduced pressure. The residue was extracted with 25 mL of ethyl acetate and neutralized with 15 mL of saturated sodium bicarbonate solution. After evaporation of ethyl acetate, the solid product methyl 3-hydroxy-4-methoxybenzoate was obtained as 9.06 g in 83.6% yield.

[1] Patent: WO2005/9389, 2005, A2. Location in patent: Page/Page column 139
[2] Patent: WO2005/9389, 2005, A2. Location in patent: Page/Page column 139
[3] Journal of Organic Chemistry, 1985, vol. 50, # 2, p. 217 - 231
[4] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 20, p. 2893 - 2897
[5] Organic and Biomolecular Chemistry, 2016, vol. 14, # 11, p. 3061 - 3068