Methyl iodide → 4-Chloro-α,α-dimethylbenzeneacetonitrile

Temperature

-15 °C

A solution of (p-chlorophenyl)acetonitrile (30.32 g, 0.20 mol) in tetrahydrofuran is treated dropwise with lithium diisopropylamide (0.44 mol, 220 mL of a 2M solution in heptane/tetrahydrofuran/benzene) at -25° C. to -30° C., over 60 minutes under nitrogen, stirred at -15° C. for one hour, treated dropwise with a solution of iodomethane (62.45 g, 0.44 mol) in tetrahydrofuran at -15° C., stirred at -15° C. for one hour, and diluted with water. The aqueous solution is extracted with ether. The organic extract is washed sequentially with water, 2N hydrochloric acid and water, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain an oily residue. The residue is distilled to give the title product as a colorless oil (32.6 g, bp 89-91° C./1 mm Hg, 90.7% yield).

1. stirringstirred at -15° C. for one hour
2. extractionThe aqueous solution is extracted with ether
3. extractionThe organic extract
4. washis washed sequentially with water, 2N hydrochloric acid and water
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated in vacuo
7. customto obtain an oily residue
8. distillationThe residue is distilled

ORD record

ord-47be2618d2714c1f961af8fa1f4176fc

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05998673