87524-66-1

67-56-1

501-89-3

87524-66-1

General procedure for the synthesis of methyl 4-carboxyphenylacetate from methanol and 4-(carboxymethyl)benzoic acid: to a solution of 4-(carboxymethyl)benzoic acid (1.00 g, 5.55 mmol, 1 eq.) in methanol (11 mL) was added thionyl chloride (0.020 mL, 0.28 mmol, 5 mol%). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure and the residue was dissolved in methyl tertiary butyl ether (MTBE). It was washed three times sequentially with saturated NaHCO3 solution and once more with water. The bicarbonate and aqueous phase extracts were combined and acidified with 1N HCl until the monomethyl ester precipitated. The mixture was extracted three times with MTBE, the organic layers were combined and dried with anhydrous Na2SO4. Concentration of the organic layer under reduced pressure afforded 4-(2-methoxy-2-oxoethyl)benzoic acid (12) (0.985 g, 91% yield) as a white solid.1H NMR (CDCl3, 400 MHz) δ 8.08 (d, 2H, J = 8.4Hz), 7.40 (d, 2H, J = 8.4Hz), 3.72 (s, 5H). The data obtained are in agreement with those reported in the literature WO2005/12220.