To a solution of diethylzinc (59 mL, 65.9 mmol) in toluene (80 mL) was sequentially added 4-acetoxystyrene (5 mL, 32.7 mmol) and diiodomethane (6.86 mL, 85 mmol). The reaction mixture was stirred at room temperature for 5 hours and then heated to reflux for 12 hours. Upon completion of the reaction, the reaction was quenched with 2N HCl solution, the organic layer was separated, washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give a brown oily crude product (4.5 g). The crude product was dissolved in methanol/tetrahydrofuran (20 mL/20 mL) mixed solvent, sodium carbonate (5.41 g, 51.1 mmol) was added, and stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and washed sequentially with saturated aqueous ammonium chloride solution and water, and the aqueous phase was back-extracted with ethyl acetate (3×). The organic phases were combined, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 4-cyclopropylphenol (3.2 g, 94% yield), the product could be used for subsequent reactions without further purification.
