8-(Benzyloxy)-8-oxooctanoic acid

Synthesis

To a solution of octanedioic acid (1 g, 5.7 mmol) and benzylic alcohol (0.31 g, 2.9 mmol) in dichloromethane (25 mL) were added 4-dimethylaminopyridine (0.39 g, 3.2 mmol) and N,N'-dicyclohexylcarbodiimide (0.66 g, 3.2 mmol). The mixture was stirred at room temperature for 1 h and concentratedin vacuo. Water (40 mL) was then added and the mixture was extracted with ethyl acetate (3 x 40 mL). The combined organic layers were washed with water (2 x 75 mL) and concentratedin vacuo. The obtained crude product was purifiedviasilica gelcolumn chromatography (cyclohexane/ethyl acetate, 80/20) affording 8-(Benzyloxy)-8-oxooctanoic acid as a translucent solid (0.545 g, 71% yield).