Hydrochloric Acid → 4-n-Butyl-2-methoxybenzoic acid

A mixture of 4-bromo-2-methoxybenzoic acid methyl ester (3.0 g, 0.0122 mole), lithium chloride (1.56 g), tetra butyl tin (4.51 g) and bis (triphenyl phosphine palladium (II) chloride (214 mg, 0.3 mmol) were heated at 100° C. for 24h. The solvent was then removed in vacuo and the residue taken up in dichloromethane. The black solid was removed by filtration and the filtrate concentrated in vacuo to give a yellow oil. The oil was purified by column chromatography (Biotage) on silica gel using 10% ether in hexane to afford a colourless oil (1.63 g). A portion of the foregoing 4-n-butyl-2-methoxybenzoic acid methyl ester (1.50 g) was dissolved in methanol (35 ml) with sodium hydroxide solution (2N, 30 ml). The mixture was allowed to stir at room temperature overnight. Then added dil. HCl until pH-5. The solvent was then removed in vacuo and the residue taken up in ethyl acethate and washed with brine. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford an oil (1.02 g).