Methyl iodide → 2,3,4,5-tetramethoxytoluene

Participants

Reaction Steps

According to a modification of the procedure by Brimble et al.,36 11 (0.660 g, 3.33 mmol) and K2CO3 (4.08 g, 29.5 mmol) were added to a flame-dried 250 mL round bottom flask followed by dry acetone (120.0 mL) and MeI (2.0 mL, 32 mmol) at room temperature. A water-jacketed reflux condenser was attached and the reaction was heated under reflux for 12 hours. The reaction was then cooled, filtered, and the solvent was removed under reduced pressure. The brown residue was then resuspended in CH2Cl2, dried over MgSO4, filtered, and condensed. The resulting colorless oil was then purified by flash chromatography (1:9 EtOAc:hexanes) to provide 6 (0.690 g, 3.25 mmol, 99%) as a colorless oil.

Provenance & Evidence