Ethyl Acetate → HCID 15953554, compound

Crotonic acid (17.2 g, 200 mmol) was dissolved in N,N-dimethylformamide (100 ml) with cooling in an ice bath under nitrogen, and powdered potassium carbonate (15.2 g, 110 mmol) was added. The mixture was stirred for 30 minutes, and 4-methoxybenzyl chloride (29.8 g, 190 mmol) was then added dropwise over 15 minutes. The reaction mixture was stirred at mom temperature for four hours and at 45° C. for 14 hours. Ethyl acetate (500 ml) and water (200 ml) were added to the reaction liquid. The separated organic layer was washed with water (100 ml×2) and brine (100 ml). The aqueous layer was extracted with ethyl acetate (100 ml). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give a crude product of the title compound (40.51 g, yield: 98.2%).

1. temperaturewith cooling in an ice bath under nitrogen
2. stirringThe reaction mixture was stirred at mom temperature for four hours and at 45° C. for 14 hours
3. washThe separated organic layer was washed with water (100 ml×2) and brine (100 ml)
4. extractionThe aqueous layer was extracted with ethyl acetate (100 ml)
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure

ORD record

ord-10b9d95ba9f740bdae376590159140fa

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476301B2