Benzyltrimethylammonium hydroxide → 3-(4-Methoxy-3-methylphenoxy)propanenitrile

A solution of 7.0 grams (0.050 mole) of 3-methyl-4-methoxyphenol (known compound) in 20 mL of acrylonitrile was stirred, and 0.4 mL of benzyltrimethylammonium hydroxide (Triton® B) was added. Upon completion of addition, the reaction mixture was warmed to reflux where it stirred during a 21 hour period. The reaction mixture was then cooled to ambient temperature and diluted with 100 mL of diethyl ether. The mixture was then first washed with three 50 mL portions of an aqueous solution of 10% potassium hydroxide, then with three 50 mL portions of aqueous 4N hydrochloric acid. The organic layer was dried with sodium sulfate, and the mixture was filtered. The filtrate was concentrated under reduced pressure, yielding 6.0 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

1. additionUpon completion of addition
2. temperaturethe reaction mixture was warmed
3. temperatureto reflux where it
4. washThe mixture was then first washed with three 50 mL portions of an aqueous solution of 10% potassium hydroxide
5. dry with materialThe organic layer was dried with sodium sulfate
6. filtrationthe mixture was filtered
7. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-2e587dcba0a4437ebf471affba0dc864

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07417057B2