Phosphorus oxide (P4O10) → 3-Methoxybenzene-1-carbonyl cyanide

m-Anisoyl cyanide was prepared according to the general procedure reported by G. A. Olah et al. [supra]. Under dry conditions, 1.686 g of m-anisoyl chloride (99%, Aldrich) (9.88 mmol), 30 mL of methylene chloride, freshly distilled from phosphorus pentoxide under nitrogen, and 1.6 mL of trimethylsilyl cyanide (12 mmol) were added to a 100-mL round bottom flask. To this solution 0.25 mL of tin (IV) chloride (2.1 mmol) was added. On addition of the tin (IV) chloride, the color of the solution changed from pale bronze to dark yellow. The solution was stirred for 2 hr at room temperature. After 2 hr of stirring the color of the solution was dark brown. The reaction mixture was quenched with 75 mL of ice-cold water and then extracted with two 75-mL portions of methylene chloride. The methylene chloride extracts were combined, washed with two 75-mL portions of ice-cold water, dried with MgSO4, and filtered. The methylene chloride was evaporated to yield 1.506 g of a dark brown oil. This oil was stirred with hot pentane. The pentane solution was decanted and the pentane was removed by rotary evaporation to yield 1.238 g (78%) of m-anisoyl cyanide as a yellow oil: IR (CCl4) (partial) 2230, 1690 cm-1.