Methanol → 2-Propenoic acid, 3-phenyl-, methyl ester

Temperature

80 °C

A mixture of cinnamic acid (25 mmol) and concentrated H2SO4 (0.1 ml) in anhydrous MeOH (25 ml) was refluxed at 80° C. (bath temperature) for 16 h. After the excess MeOH was removed by a rotary evaporator, the residue was treated with H2O (50 ml), and the resulting mixture was extracted with EtOAc (3×50 ml). The combined extracts were washed with H2O (50 ml) and brine (50 ml), and dried (anhydrous Na2SO4). The solvent was evaporated to dryness, and the crude products were purified by flash silica gel chromatography (eluting with 10-60% hexane in EtOAc) to afford methyl cinnamate.

1. customAfter the excess MeOH was removed by a rotary evaporator
2. additionthe residue was treated with H2O (50 ml)
3. extractionthe resulting mixture was extracted with EtOAc (3×50 ml)
4. washThe combined extracts were washed with H2O (50 ml) and brine (50 ml)
5. dry with materialdried (anhydrous Na2SO4)
6. customThe solvent was evaporated to dryness
7. customthe crude products were purified by flash silica gel chromatography (eluting with 10-60% hexane in EtOAc)

ORD record

ord-bc67c5b28f3643f3b0ba03b4c5019650

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260382B2