Potassium Iodide → 3-Cyclopentyloxy-4-methoxybenzaldehyde

Participants

Reaction Steps

To a solution of 54.9 g (0.36 mol) of 3-hydroxy-4-methoxybenzaldehyde in 400 mL of absolute ethanol was added 40.4 g (0.72 mol) of potassium hydroxide, 1.0 g (0.01 mol) of potassium iodide, and 77.0 mL (0.72 mol) of cyclopentyl bromide. The mixture was warmed to reflux for 48 hours at the end of which time the completed reaction was cooled to room temperature and concentrated to a syrup. The resulting residue was dissolved in 500 ml of ethyl acetate, washed with one, 100-mL portion of water, with one, 50-mL portion of dilute hydrochloric acid, with one, 100-mL portion of saturated sodium bicarbonate, and with one, 50-mL portion of saturated sodium chloride. The organic fraction was dried over sodium sulfate and concentrated to dryness. The amber syrup was liquid chromatographed over 500 g of silica gel using 20% ethyl ether in hexane as an eluent to provide the analytically pure oil upon drying in vacuo.

Provenance & Evidence