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 The
3. extractionorganic 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-b1163cb644d04cccbd842eb64d1bec24

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05849958