Synthesis
The general procedure for the synthesis of methyl 2-(2-methoxy-2-oxoethyl)benzoate and 2-(2-methoxy-2-oxoethyl)benzoic acid from methanol and o-carboxybenzeneacetic acid was as follows: o-carboxybenzeneacetic acid (2.01 g, 10.0 mmol) was dissolved in methanol (10 mL), and the resultant solution was transferred to a syringe and mounted on a syringe pump. This methanol solution was pumped at a flow rate of 0.177 mL/min into a stainless steel column (4.0 mm ID x 50 mm length, 0.53 mL internal volume) filled with HO-SAS (334 mg). The column was immersed in an oil bath preheated to 110 °C and a back pressure regulator was connected to maintain the system pressure at 75 psi.The reaction effluent was discarded during the initial 10 min of the reaction, followed by the collection of the reaction mixture over 3 min and the addition of n-decane as an internal standard for the gas chromatographic analysis. The reaction effluent was continued to be collected in a glass flask for 30 min, after which the solvent was removed by rotary evaporation. The crude product was purified by silica gel fast column chromatography (eluent ratio hexane/ethyl acetate = 5/1) to give the final target product methyl 2-(2-methoxy-2-oxoethyl)benzoate (1.13 g, 99% yield).
References
[1] Journal of Chemical Research - Part S, 2000, # 6, p. 282 - 283
[2] Bulletin of the Chemical Society of Japan, 2017, vol. 90, # 5, p. 607 - 612
[3] Tetrahedron Letters, 2003, vol. 44, # 51, p. 9205 - 9208
[4] Journal of the Indian Chemical Society, 1987, vol. 64, # 1, p. 34 - 37
