Methyl iodide → 2-Isopropylanisole

Participants

Reaction Steps

To a stirred 20° C. solution comprised of KOH (1154 g, 4.75 mol), Bu4N+ HSO4− (140 g, 0.41 mol) in H2O (5.6 L) was added commercially available 2-isopropylphenol (590 g, 4.33 mol) in CH2Cl2 (5.6 L). After 30 min, MeI (741 g, 5.22 mol) was added prior to stirring the reaction overnight. After separation of the layers, Et3N (185 mL, 1.3 mol) was added to the CH2Cl2 fraction to destroy the residual MeI. After 15 min, the CH2Cl2 was removed under vacuum and the salts suspended in cyclohexane (4 L) prior to filtration. The cyclohexane filtrate was sequentially washed with 2N HCl followed by 2 brine washes. Concentration under vacuum yielded 2-isopropylanisole (612 g, 94%) as a light yellow oil.

Provenance & Evidence