Synthesis
General procedure for the synthesis of methyl 2-methoxy-6-methylbenzoate from 2-methoxy-6-methylbenzoic acid and iodomethane: To a solution of 2-methoxy-6-methylbenzoic acid (1.0 eq.) in N,N-dimethylformamide (DMF, 3.8 mL/mmol 2-methoxy-6-methylbenzoic acid) was added iodomethane (3.0-6.0 eq.) and potassium carbonate ( K2CO3, 2.5-5.0 eq.). The reaction mixture was heated to 70 °C and stirred for 17-18 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the reaction was quenched by addition of water (H2O). The organic phase was extracted with ethyl acetate (EtOAc), the organic layers were combined, dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure in a fume hood to give the target product methyl 2-methoxy-6-methylbenzoate. Precautions: Iodomethane is toxic and carcinogenic, the operation should wear gloves and be carried out in a well-ventilated fume hood.
References
[1] Tetrahedron, 2018, vol. 74, # 2, p. 224 - 239
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 360 - 365
