N-(4-Methoxyphenyl)Acetamide → N-(4-methoxyphenyl)-N-(2-methylallyl)acetamide

Participants

Reaction Conditions

Reaction Steps

To a solution of p-acetanisidide (1.00 g, 6.05 mmol), potassium carbonate (0.92 g, 6.7 mmol), sodium hydroxide (0.27 g, 6.8 mmol) and tetra-n-butylammoniumbromide (0.39 g, 1.2 mmol) in 10 mL of toluene was added 3-chloro-2-methyl-1-propene (0.71 mL, 7.3 mmol) at room temperature. After the reaction mixture was stirred at 75° C. for 4 h, the reaction mixture was cooled to room temperature, and was diluted with ethyl acetate. The solution was washed with water, 3 M HCl, saturated NaHCO3 aqueous solution and brine, successively, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 60/40) to obtain the title compound (1.26 g, 95%).

Provenance & Evidence