Chemical Properties
white to light yellow crystalline powder
Uses
Methyl 4-methoxysalicylate (methyl 2-hydroxy-4-methoxybenzoate) was used in the enantioselective synthesis of (+)-coriandrone A and B, two bioactive natural products.
Synthesis
General procedure for the synthesis of methyl 4-methoxysalicylate from methyl 4-methoxybenzoate: Ru(MesCO2)(L) (p-cymene) [L=2,2'-bipyridine or 4,4'-dibromo bipyridine] (2.5 mol%), oxidizing agent (2.0 eq.), and methyl 4-methoxybenzoate (1.0 eq.) were added to a sealed tube. Subsequently, a mixture of trifluoroacetic acid (TFA) and trifluoroacetic anhydride (TFAA) in the ratio of 0.6 mL:0.4 was added. The reaction mixture was placed in an oil bath preheated to 110 °C and stirred until the reaction was complete, and the reaction process was continuously monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was quenched by the addition of ice water and extracted with dichloromethane. The organic layer was dried with anhydrous sodium sulfate (Na2SO4) and subsequently concentrated by rotary evaporator. Finally, the residue was purified by silica gel column chromatography to afford the target product methyl 4-methoxysalicylate.
References
[1] Tetrahedron Letters, 2017, vol. 58, # 38, p. 3743 - 3746
