Potassium Carbonate → Methyl 3-(cyanomethoxy)benzoate

Temperature

60 °C

To a solution of methyl 3-hydroxybenzoate (5.00 g, 32.9 mmol) in acetone (60 mL) were added bromoacetonitrile (2.63 mL, 39.4 mmol) and potassium carbonate (6.81 g, 49.3 mmol), and the mixture was stirred at 60° C. for 4 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution (100 mL), and the mixture was extracted with ethyl acetate (100 mL, 30 mL). The combined organic layer was washed with saturated brine (10 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=90/10→80/20), and fractions containing the object product were concentrated under reduced pressure to give the title compound (5.43 g, 86%) as a colorless oil.

1. extractionthe mixture was extracted with ethyl acetate (100 mL, 30 mL)
2. washThe combined organic layer was washed with saturated brine (10 mL)
3. dry with materialdried over anhydrous magnesium sulfate
4. filtrationThe insoluble material was filtered off
5. concentrationthe filtrate was concentrated under reduced pressure
6. customThe obtained residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=90/10→80/20), and fractions
7. additioncontaining the object product
8. concentrationwere concentrated under reduced pressure

ORD record

ord-254488ea0e6647c8bfcaa00f73c59c3d

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344135B2