2-Cyclopentyl-2-hydroxyphenylacetic acid (4.47 g, 20 mmol) and potassium carbonate (7.01 g, 50 mmol) were dissolved in N,N-dimethylformamide (50 mL). Iodomethane (8.64 g, 60 mmol) was slowly added to the mixture at room temperature. The reaction mixture was stirred continuously for 2 hours at room temperature. Upon completion of the reaction, the mixture was poured into water and extracted three times with hexane. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with the eluent being a 1.5:1 solvent mixture of hexane and dichloromethane, resulting in the pure product methyl 2-cyclopentyl-2-hydroxyphenylacetate (3.02 g, 64% yield). The structure of the product was confirmed by 1H NMR (CDCl3, 300 MHz): δ 1.32-1.37, 1.43-1.69 [8H, m, (CH2)4], 2.90 [1H, p, CHC(OH)], 3.74 (1H, s, OH), 3.77 (3H, s, CH3), 7.25-7.37, 7.63-7.65 (5H, m, Ph) ppm.
