Dimethyl Sulfate → 3-Methoxy-2-phenylacrylonitrile

3-Hydroxy-2-phenylacrylonitrile (12.3 g, 84.7 mmol) was dissolved in dry THF (100 ml) in a reaction vessel, and then NaH (4.1 g, 169.4 mmol) was slowly added thereto. The mixture was stirred at room temperature for 2 hr. Thereafter, dimethyl sulfate (13.7 ml, 144.0 mmol) was added, followed by stirring at 40° C. for 12 hr. After completion of the reaction, the reaction mixture was washed with distilled water and concentrated under reduced pressure. The concentrate was diluted with EtOAc and extracted with EtOAc together with distilled water. The organic layer was dried over anhydrous MgSO4 and filtered. The filtrate was concentrated under reduced pressure to give 17.9 g (112.5 mmol, quant.) of the title compound.

1. stirringby stirring at 40° C. for 12 hr
2. customAfter completion of the reaction
3. washthe reaction mixture was washed with distilled water
4. concentrationconcentrated under reduced pressure
5. additionThe concentrate was diluted with EtOAc
6. extractionextracted with EtOAc together with distilled water
7. dry with materialThe organic layer was dried over anhydrous MgSO4
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-4e918329aedb4a6db664e41000b0f177

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260448B2