Water → HCID 66905801, compound

A mixture of 2-hydroxy-3-(4-nitrophenyl)acrylic acid (15 g, 71.7 mmol), cesium carbonate (56 g, 172.1 mmol) and dimethyl sulphate (14.2 ml, 150.6 mmol) in DMF (270 ml) was stirred at RT for 18 hr. Water (220 ml) and ethyl acetate (150 ml) were added and the layers separated. The aqueous layer was further extracted with ethyl acetate (4×100 ml) then the combined organics were washed with water (6×100 ml), brine (2×120 ml) and concentrated to half volume. Heptane was added (70 ml) and the mixture concentrated to 200 ml volume. The resulting precipitated solid was collected by filtration, washed with heptane (2×100 ml) and suction dried on the filter to afford methyl 2-methoxy-3-(4-nitrophenyl)acrylate as a tan solid (9.2 g, 54% yield) containing a trace of heptane.

1. customthe layers separated
2. extractionThe aqueous layer was further extracted with ethyl acetate (4×100 ml)
3. washthe combined organics were washed with water (6×100 ml), brine (2×120 ml)
4. concentrationconcentrated to half volume
5. additionHeptane was added (70 ml)
6. concentrationthe mixture concentrated to 200 ml volume
7. customThe resulting precipitated solid
8. filtrationwas collected by filtration
9. washwashed with heptane (2×100 ml) and suction
10. customdried on the
11. filtrationfilter

ORD record

ord-2bd718ae2b8b40bbaab0ea2a8094b44c

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09345680B2