p-Anisoyl chloride → 4-methoxybenzoyl cyanide

p-Anisoyl cyanide was prepared according to the general procedure reported by G. A. Olah et al. [supra]. Under dry conditions, 1.8740 g of p-anisoyl chloride (99%, Aldrich) (10.98 mmol), 30 mL of methylene chloride, freshly distilled from phosphorus pentoxide under nitrogen, and 1.7 mL of trimethylsilyl cyanide (13 mmol) were added to a 100-mL round bottom flask. To this solution, 0.27 mL of tin (IV) chloride (2.3 mmol) was added. The reaction was stirred for 2 hr at room temperature. During the 2 hr, the color of the solution changed from clear to dark brown. After the 2 hr of stirring, the reaction 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 removed by rotary evaporation to yield 1.592 g (90%) of p-anisoyl cyanide as a dark orange solid: IR (CHCl3) (partial) 3020, 2220, 1675, 1600 cm-1.

1. customp-Anisoyl cyanide was prepared
2. customDuring the 2 hr
3. stirringAfter the 2 hr of stirring
4. customthe reaction was quenched with 75 mL of ice-cold water
5. extractionextracted with two 75-mL portions of methylene chloride
6. washwashed with two 75-mL portions of ice-cold water
7. dry with materialdried with MgSO4
8. filtrationfiltered
9. customThe methylene chloride was removed by rotary evaporation

ORD record

ord-13557264a87a40579619295f0474750a

Source dataset

uspto-grants-1990_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04942247