Benzyl Alcohol → 3,5-Dimethylbenzonitrile

Temperature

110 °C

An oven dried screw cap test tube was charged with NaCN (140 mg, 2.857 mmol) dried KI (79 mg, 0.476 mmol, 20 mol %) and CuI (45 mg, 0.236 mmol, 10 mol %), evacuated and backfilled with argon three times. Anhydrous toluene (1550 μl), N,N′-dimethylethylenediamine (255 μl, 2.395 mmol), 1-Bromo-3,5-dimethyl-benzene (255 μl, 1.877 mmol), and benzyl alcohol (155 μl, 1.498 mmol) were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 12 h. The resulting yellow color suspension was cooled to room temperature, 2 mL of ethyl acetate, 250 μl of n-dodecane as internal standard, 1 mL of ammonium hydroxide 30% and 1 mL of water were added. The mixture was stirred at 25° C. for 10 min then the organic layer was washed with 1 mL of water and dried over MgSO4. The GC analysis showed a conversion of 91% with a yield of the title product, calculated vs internal standard, of 88%.

1. customAn oven dried screw
2. customcap test tube
3. customevacuated
4. customThe tube was sealed
5. temperatureThe resulting yellow color suspension was cooled to room temperature
6. stirringThe mixture was stirred at 25° C. for 10 min
7. washthe organic layer was washed with 1 mL of water
8. dry with materialdried over MgSO4

ORD record

ord-891b035f5df047dd86484f892ee2fc1a

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07323608B2