Methyl iodide → 2-(4-Methoxyphenyl)propanenitrile

Temperature

-78 °C

14.7 g (0.10 mole) of p-methoxyphenylacetonitrile was dissolved in 250 ml of dry tetrahyrofuran and placed in a dry ice/isopropanol bath under N2. 69.0 ml of 1.6M n-butyl lithium (0.11 mole) was added dropwise over 30 minutes and the mixture stirred at -78° C. for one hour. The lithium salt of the nitrile precipitated as a yellow solid during this time. 71.0 g (0.50 mole) of methyl iodide was then added and stirring at -78° C. continued for an additional hour. The mixture was then poured into saturated ammonium chloride and the product extracted into diethyl ether, washed with saturated sodium chloride and dried over sodium sulfide. It was filtered and evaporated, redissolved in methylene chloride and passed through Florisel®. Evaporation gave 15.0 g of α-(p-methoxyphenyl)propionitrile as an orange oil.

1. customplaced in a dry ice/isopropanol bath under N2
2. customThe lithium salt of the nitrile precipitated as a yellow solid during this time
3. stirringstirring at -78° C.
4. waitcontinued for an additional hour
5. extractionthe product extracted into diethyl ether
6. washwashed with saturated sodium chloride
7. dry with materialdried over sodium sulfide
8. filtrationIt was filtered
9. customevaporated
10. dissolutionredissolved in methylene chloride
11. customEvaporation

ORD record

ord-6b01b1ff67b242eeb1220a093aec4308

Source dataset

uspto-grants-1985_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04535186