Dimethyl Sulfate → 2,6-Dimethylanisole

Participants

Reaction Conditions

Reaction Steps

Sodium hydroxide (20 g, 500 mmol) was dissolved in distilled water (200 mL) and placed in a round-bottom flask fitted with a reflux condenser. To the solution were added sequentially 2,6-dimethylphenol (1, 61 g, 500 mmol) and dimethyl sulfate (48 mL, 500 mmol). The mixture was heated at 60° C. for about 17 h, cooled, and transferred to a separatory funnel. The organic layer was separated, and the aqueous layer was extracted with benzene. The combined organic layers were washed sequentially with 10% aq. sodium hydroxide and brine, and dried (MgSO4). Concentration of the solution gave 2,6-dimethylanisole (2, 39 g, 57% yield), bp 179°-182° C./750 torr (lit.: Burton, G. W.; Joyce, A.; Ingold, K. U. Arch. Biochem. Biophys., 1982, 221, 281; 181° C.), as a colorless oil.

Provenance & Evidence