Methyl iodide → 2-Isopropylanisole

Participants

Reaction Steps

To a solution of 2-isopropylphenol (30 g, 220.3 mmol) in CH2Cl2 (300 mL) was added tetrabutylammonium hydrogen sulfate (7.5 g, 22.1 mmol). After the entire solid was dissolved, a solution of potassium hydroxide (61.8 g, 1.1 mol in 300 mL H2O) was added to the previous mixture. After 15 minutes of stirring, methyl iodide (47 g, 20.6 mL, 331 mmol) was added. The mixture was left to stir overnight (ca. 15 hours). The organic layer was separated and then washed with brine (2×100 mL), dried (Na2SO4), filtered and concentrated in vacuo. The solid material in the concentrate was removed by filtration. The precipitate was washed with hexane (100 mL). The filtrate was concentrated in vacuo to give 32.15 g of yellow oil as a crude product. The crude product was filtered through a pad of silica gel (250 g) and washed with 5% EtOAc in hexane to give 30.7 g (93%) of compound 1a as a colorless oil.

Provenance & Evidence