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4-Heptylbenzoyl cyanide was synthesized according to the general procedure reported by G. A. Olah et al [supra]. Under dry conditions, 2.5518 g of 4-heptylbenzoyl chloride (99%, Aldrich) (10.69 mmol), 30 mL of methylene chloride, freshly distilled from phosphorus pentoxide under nitrogen, and 1.65 mL of trimethylsilyl cyanide (12 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 mixture was stirred for 2 hr at room temperature. During the 2 hr, the color of the solution changed from a pale yellow to dark brown. After 2 hr of stirring, the reaction was quenched with 81 mL of ice-cold water and then extracted with two 81-mL portions of methylene chloride. The methylene chloride extracts were combined, washed with two 81-mL portions of ice-cold water, dried with MgSO4, and filtered. The methylene chloride was removed by rotary evaporation to yield 2.097 g of a dark brown oil. This oil was distilled at 106°-109.5° C. (0.2 mm) to yield 1.214 g (50%) of 4-heptylbenzoyl cyanide as a colorless oil that solidified on standing in the freezer: IR (CCl4) (partial) 2930, 2860, 2220, 1680, 1610 cm-1.

1. customDuring the 2 hr
2. stirringAfter 2 hr of stirring
3. customthe reaction was quenched with 81 mL of ice-cold water
4. extractionextracted with two 81-mL portions of methylene chloride
5. washwashed with two 81-mL portions of ice-cold water
6. dry with materialdried with MgSO4
7. filtrationfiltered
8. customThe methylene chloride was removed by rotary evaporation